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Eddie
Welcome back, Canal Street Dreams. As you just witnessed, our man ID'd the top studio Nicholson in the house today. But I've known Jake since about 2010. I think you did like a curated fashion thing at like Wieden and Kennedy.
Jake
Dude, I just, I just. So I was at dinner with. With James Harris at this Converse event on Tuesday night, and I totally forgot that that's where we actually met was at that Wieden and Kennedy thing. Because I think that's where I first met James too.
Eddie
Oh, word?
Jake
Yeah.
Eddie
No way.
Jake
Yeah.
Eddie
I didn't even meet James there. I met you.
Jake
Yeah.
Eddie
Because I think you put me on the Berkman Bros.
Jake
Correct. That's where I was an intern at the time. Yeah, yeah, yeah.
Eddie
And I bought shorts from you. And I think you put me on the Highland at the time. There was like a Highland designer. There was a map. There was like, it was the booth next to you and this woman had a brand called Highland and she had a shirt that was the map of the world.
Jake
Okay.
Eddie
And I was like, I need that. I started rocking it on Wong's World back in the day. So that's where I met you, I think.
Jake
Yeah, you were doing like a bow House. Like you were doing like you were serving bows at the White and Kennedy event. Yeah, yeah, yeah.
Eddie
Okay.
Jake
Yeah, yeah, yeah.
Eddie
Phil Chang. But us, all those attack guys, like, you know, Larry, because they had done.
Jake
The reason that, that we were connected to Phil is because they had done a. For Berkman Bros. The company that I was interning, it was like my first fashion job. Phil and his crew, they had done a, like a stop motion video for the brand. And so that's how they got connected with them. And then, yes, when they were doing this event, they like invited us to do the event. Word.
Eddie
How'd you get into fat? Like, tell us the whole story.
Jake
So I was like got. I was always into like what I wore as a kid. I mean, it literally like not to get too therapy about it, but it was like.
Eddie
Get therapy?
Jake
Yeah. As like a three year old, you know, I wore costumes every day, like superhero costumes and stuff. So like I loved like I wore like a super costume like every day. And so I just always like dressing up and like the feeling of like, I mean, it really is like similar to fashion is like you put on clothes and you sort of assume a character. And so, you know, you know, very, very early on and then just always kind of cared what I, what I wore.
Eddie
I thought I was Omar Epps.
Jake
Yeah.
Eddie
I shared was like I'm Omar Epps from Love and Basketball.
Jake
Exactly.
Natasha
Omar Epps, slash Aaron Hernandez is what we. Is what we've recently Not. Not by action, but by bye bye vibe.
Eddie
Vibe. She was like, your vibe.
Natasha
Your style is like, specifically when he got arrested. And he has the white T shirt on, but his hands are in the cuff, but the white T shirt is still on the body. That's very you. And he had a very clean haircut at the tattoo. When I look at you and I think if Eddie were a white man or, like, Latino, I think you're like, you would look like Aaron Hernandez.
Eddie
I like it. I like it.
Natasha
I would just fly for you because that's one of the hottest man I've ever seen in my whole entire life. Aaron Hernandez. Like, I saw him and I was like, I think I like dick. I think I like men. I think I want to. I think I want to have men in my life.
Eddie
Aaron Hernandez turned her out.
Natasha
It was a sexual awakening for me. Previous to that, I thought I was interested in women. And I was like, that was one of the men where I was like, I think I like men.
Eddie
He fly. Aaron Hernandez fly. I also wore a lot of fogging double XL white tees, was rolling around Orlando basketball shorts, white tees, flip flops, and socks.
Jake
I was having a conversation with someone recently about just, like, remembering the era of Foot Locker when you'd go, and they had the regular T shirts and then the tall T section. Yeah, I remember I. Because I got, like, probably in 2004, I got, like, a pink, tall tee at Foot Locker. And that was so. That was. That was an era for me.
Natasha
Yeah, Tall teas are great.
Eddie
Who are you channeling with that Cameron, probably.
Jake
Yes, yes.
Eddie
The God.
Jake
Yeah, exactly. But then she used to dress up.
Eddie
A lot as a kid. I want to continue the story. But you used to dress up a lot.
Natasha
Yeah, I used to dress up as a cat. I mean, the running joke in our family was like, she's gonna be a stripper. Because I would take, like, the neck guard from when you would go ski skiing and wear it as a mini skirt and, like, go show my family. I would dress up as Christina Aguilera. I would put, like, gems on my here and here. I was like, always. I was always. And, like, I would steal thongs from Victoria's Secret with my. When we. My mom would go, I would steal red lacy thongs and dress up in them. So, like, I also knew. I was like, I'm gonna. I'm gonna be naked when I get Older, fashion wise. Like, I knew my. I knew the reference. Like, I was young and I was like, oh, you can be that. You could do that. You could, like, choose. You could, like, use your sexual power.
Jake
You did.
Natasha
I knew from a very young age.
Eddie
Yeah.
Natasha
And I loved it. I, like, leaned in. Like, I was always in, like, a cat outfit.
Eddie
Yeah, I love it too, because it's like, what you're talking about. We literally witnessed this week. We dropped our son off for his, like, first day of pre preschool, and there was a kid that came as Spider Man.
Jake
Exactly.
Eddie
And I was like, it's so cute, man.
Natasha
But that was so ill because all the kids were very emotional. Like, it's the first day of school, they're dropping off, they don't want to leave mom and dad. They're scared. And I was like, that kid's so cool. He doesn't even know that by him dressing up as Spider man, he's, like, comforting the other kids. Because I said to our son, I said, look, it's Spider Man. And he was like, oh. And, like, kind of stop crying for a second. And I was like, that was like, that kid doesn't even know what he's doing for his peers. Like, comforting them.
Jake
Totally.
Natasha
You know, that's really cool. Psychologically, like, become a parent yourself and be like, no, the Spider man kid is so ill. Thank you for that.
Eddie
You were a hero.
Jake
Yeah.
Natasha
You comforted all the kids.
Jake
I had, like, these. And I was like, these red rain boots that went with it. Cause, like, the costume didn't come with, like, booties, you know, it was just like pajama style with, like a velcro cape. And then so I wore, like, red rain boots to, like, finish it off.
Natasha
I had a red rain boot phase.
Jake
Yeah.
Natasha
My mom always tells me, she's like, you had these red rain boots. You wouldn't take them off.
Jake
Yeah, I was the same way. Like, literally couldn't go. Couldn't go anywhere without those. But like, even, like later, like, I remember, you know, like, I played basketball as a. As a kid, just like rec league or whatever. But like, my favorite. Thinking back, like, the most excited part of that whole new basketball season for me was getting new sneakers. You know what I mean? But my parents had a rule that I wasn't allowed to wear the sneakers anywhere but the court during the season. And then once the season was over, I got to deploy them out in the real world.
Eddie
Working class family.
Jake
I mean, we're upper middle class up in Connecticut.
Eddie
Yeah, yeah, yeah. No shit. No shit. I Was just curious, like, because my parents were like, you got to wear the same shoes for basketball and outside. And then I was just, like, brushing them and washing the bottoms. But I liked it. Your parents were smart because, like, this is performance.
Jake
Like, exactly.
Eddie
I wanted that to be, like, separate. Like, I need airwalks to walk around, and I need Jordan fives to play ball. And, like, you're going to. You're actually just going to get flights, and you're going to do everything in them.
Jake
Yeah. So, like, and it was a thing where, you know, you had, like, the little mini, like, Thai backpack. So I would, like, put my. The first pair that I was very excited about that I got were Iversons, but they were question answer fours, so they were white and red answer fours. I hope I'm getting the numbers right. They were white and red answer fours. And then, so, yeah, during the season, I would put them in my little backpack, get to the court, you know, and it's like in the winter in Connecticut. So, like, it actually was smart. Cause, again, like, the ground was gross. They would have got dirty so fast. So they got to stay clean all season long. And then after that, like, it was like, I got the. The T. Mac twos and then the T. Mac threes, and, like, so. So whatever, you know, like, obviously, I love, like, most people, I love Air Jordans. But when I think back to, like, the shoes that were important to me as a kid, it was Iverson's, and T. Macs were the ones. Because I was, you know, 10, 11, 12 years old when those came out, bro.
Eddie
I used to think I had, like, super abilities with the new shoes. Like, I would read the specs, like, oh, I'm gonna be ill this year.
Jake
Yeah.
Eddie
And I remember I got the T. Mac ones, and I was so hype. I was balling in the T. Mac ones, and. And I was beating my dad, and it was one of the first times I was beating my dad in basketball, and this motherfucker pushed me, and I sprained my ankle, and I was like, I hate you, man. Yeah. Like, it's the worst.
Jake
Come on, TMac.
Eddie
It's the worst ever, man. Oh, no. I was more mad at my dad.
Jake
Oh, you're mad at your dad? Thought you're mad at tmac.
Natasha
I was just beating.
Eddie
I was like, dude, TMAC was making me so much iller. The shoes. My dad just pushed me in a bush, and I sprained my ankle. I'm like, bro, what's wrong with you?
Natasha
It's such a traumatizing Story. I'm so sorry.
Jake
I, like, remember it. Yeah, he's like, you're not. You're not getting. You're not winning today.
Eddie
And that's my dad.
Jake
Yeah, that's really funny.
Natasha
For the girlies, we had the V shoes. Something I was really excited to get as a young girl was the. We have to insert a picture because I, like, need to just do this. For the girlies. It was a platform rocket dog. That. It wasn't a rocket dog. It was. It was, like volatile or something was the name of it. And it had a V on it, and it was a platform shoe. And it almost just looked like you were wearing a boat, but it was so platformed. And I was already, like, a tall girl. And like, all my, like, cutie short, like, girls, girlfriends with, like, mini Abercrombie shorts were getting them. And my mom, I remember, was just like, you're, like, already tall. You, like, don't need the 4 inch platform sneaker. And I was like, okay. And also the fat Farm sneakers that had the little spinner in it. I had pink ones with little Fat Farm spinners.
Jake
There was Fat Farm spinners because obviously I know those data.
Natasha
Yes. But it was a fat farm. They, like, did that for, like, I had a. It was pink and white, and they had just a little silver, like, insert on the side that just had, like, a little spinny thing. And I will find a photo because they were like. I was so excited to get both of those shoes.
Eddie
Yeah. Spinning sneakers was, like, a great evolution.
Jake
So cool. Like, maybe one kid in my school had a pair, and obviously he was, like, the coolest.
Eddie
I just remember even I was in Orlando, Florida. So everybody. Everybody had.
Jake
Yeah. The standard was. Yeah. I grew up in Newtown, Connecticut. Oh, yeah? Yeah, yeah.
Eddie
Okay, cool. If you were in Hartford, everybody had this.
Jake
Everybody.
Eddie
There was like, a Hartford, Orlando connection. There always Italian dudes or, like, Puerto Rican Dominican dudes from Hartford in Orlando. And we all just dressed the same. Insanity.
Jake
I just remember also, like, the East Bay catalog, and then they had all the different colors of the dadas, you know, like, it was like. And they were. Because, like, I guess the whole idea was that you could get them for your team, you know, like your team. The whole team could get spinners. That's so cool. You know, so they had the catalog, and it was like they had all the sort of color combos laid out, and they were all, like, very shiny patent leather sneakers. And they were like, you know, blue and black or, like red and green. Like, whatever color combo you Wanted you get in the data.
Eddie
Yeah, that was my style. Like, I. New Balance was the ugliest shit to me. And then one year, they put out New Balance with patent leather, and I got every color. And, like, the preppier kids at school were like, that's not how you rock it. I'm like, no, that's how I rock it. I want to see myself in my shoe.
Jake
Yeah.
Natasha
Yeah, that's how I rock.
Eddie
Picture myself rolling in this shoe.
Natasha
That sounds like also just, like, an early 2000s ad. Like, that's how I rock it.
Eddie
I should have been a copywriter for Lux. Like, for real.
Natasha
That would have been the commercial. I've seen it.
Eddie
Yeah.
Natasha
In my head.
Eddie
Yes.
Jake
Yeah. So, like, I guess, you know, like, I always just had an interest in it. Like, always, like, enjoyed, you know, sneakers and clothes. Like, again, that was always just, like, a fun day. Day before school, going to the mall and, like, getting new clothes or, like, for basketball season or whatever. And then in high school, I guess is when I, like, started, you know, reading websites like Hypebeast. And. And @ the same time that I was reading going on Hypebeast every day is when I started, like, looking at GQ magazine and sort of, you know, so I had these sort of two parallel things where it'd be like. I remember in high school, like, buying, like, this kid named Vinnie, and he, like, sold sneakers out of the trunk of his car, and I bought a pair of, like, Air Max 95s from him out of the trunk of his car at the high school parking lot. But then at the same time, I was, like, going to J. Crew and, like, buying, like, pea coats and stuff. So, like, it was. I had both of those things going. And, like, then high school, you know, that was when Kanye had, like, Kanye University. And so I would check his blog every day. And so, like, the menswear and fashion thing just sort of picked up from there. And then. And then, like, by the time I met you, it was like, I had already, you know, decided that I wanted to be in menswear and fashion. And then I had, like. The way that I got that job was actually funny. Was, like, I was going to school in Philadelphia at the time, at Temple University. I went to school thinking I was gonna be a film major, and then realized very quickly that I didn't actually want to do that. But there was a Barney's Co op in Written House Square in Philly.
Eddie
Shout out Barney's.
Jake
Yeah. Shout out Barney.
Eddie
Bring back Barney.
Jake
Yeah. I got to read the new Book that just. That just came out about. About the whole saga.
Eddie
We just want Barney's back.
Natasha
Me too. I want to play Go to Feel Good Again.
Eddie
Like, that was the peak department store for sure.
Jake
You know, it was the coolest one. It was the one that had all.
Eddie
The best stuff, you know, like, respect, Ronnie Fag. But we need Barney's and we need opening ceremony back, you know?
Jake
Opening ceremony. Yeah. Wow.
Eddie
Please.
Jake
Yeah.
Eddie
Please. Sorry.
Jake
No, no, no, no. And so I. Basically, all we got is chcm, which we love. Shout out to Sweet, too.
Eddie
Yeah, yeah. But it's like, Sweet Too needs a department store. Somebody needs to bankroll the Sweetu department store.
Jake
Like, give him a bigger venue. Yeah.
Eddie
I'm like, that dude is an artist. Like, truly an artist. But, like, continue.
Jake
Yeah, yeah. And also, just the CHM sidebar. Just, like, you know, as far as independent small retailers, the fact that he's been doing it since 08 and it's still around is, like. Is not a small feat, I don't think. To be like, a small store, you know, in the basement on Bond street and, like, just still be going 17 years later is like. I mean, shout out.
Eddie
Let's just get into a Sweet too, to me, is like the record shop of menswear.
Jake
Yeah.
Eddie
Every other creative director buyer in the world in menswear goes to see what Sweetie is buying.
Jake
Yeah.
Eddie
And, like, you can see it at every other store. I ain't going to even shout out names. They're doing his thing. They're cribbing it, they're sampling it. But people don't give him credit unless, like, you're ahead in downtown New York for sure.
Jake
And he's one of the most humble people, too. So I don't even know if he, like, necessarily even thinks things in those terms, you know, if, like, wanting credit or anything. He just, like. But he is super, super influential in terms of, like, you know, I'm so. I'm so online and tapped into, like, every brand. I have so much information, you know, coming in, like, into my brain about menswear all the time. CHCM is like, one of the few places that I'll go and be like, I have no idea what this brand is, you know, despite the fact that we live in 2025 and all the information, the world's out there. Like, that's so cool to me that there's still a space out there where, you know, people like me who work in the industry can go and be like, I literally have never heard of this brand. Like, can you tell me about it, you know, and you know, that's just a testament to like how he is always soldier.
Eddie
Yeah, I'm a sweet tooth soldier because I've been shopping there for a minute. And it was Simone as Wolf, who was also legendary stylist, I believe the original stylist at Complex magazine when, like Bradley Carbone and all them were there. Like, he's the one that took me to CHCM and was like, yo, shop here. And I was like, oh, this shit crazy. Yeah, like this shit really fly. But yeah, man, it's. It's like a. It's. It's one of those things is the person who's actually passionate and wants to do it the right way, never scaling doesn't come into their mind.
Jake
Yeah.
Eddie
And someone else who doesn't have that passion and doesn't have that like truth running through them will bite it and.
Jake
Then water it down and try and try and extrapolate whatever it is that Sweetu is doing into like some sort of bigger thing. And maybe that's part of like, maybe you can't do that. Maybe it's so like the fact that it is small and run by one guy who, you know, you go in there and sweet too will literally be steaming clothes and taking pictures of them for the website to this day.
Eddie
And the homies that make beats in there selling the clothes are the best, you know, like, those are my guys.
Jake
Yeah. And they're all like super knowledgeable and passionate about product too. And that's what's just. And you feel that as a customer, I mean, I will say, like, you go effortless way. Yeah.
Eddie
Knowledgeable in an effortless way. You'll go, you three. No, son, you a four. Yeah. I don't know. Like, those are the stylists I talk to for sure.
Jake
And I'll just say, if you haven't been to CHM before anyone out there, like, if, you know, I wouldn't expect like, you know, Ralph Lauren level hospitality when you walk in the store. But like, it's not like no one's being mean. They're just like sat beats. Yeah. It's just, it's just like, you know, you walk in and then if you have questions, they'll. They'll help you. And they're super knowledgeable.
Natasha
They're cool because even when he's shopping, like, I can kick it with them and like sit on the little bench and talk to them and chat with them. And that's. Sometimes I think when you're in for a woman and when you go into, like, a menswear space. Exclusively menswear. Like, everybody's a little too cool and, like, her. She doesn't. But they're really cool to me. And I. I like going in there with you because even I know, I'm like, what's up? How are you? What's going on? And they're just, like, so warm and welcoming.
Eddie
Yeah. Because in the industry, I know what you're saying, like, the. The Ralph Lauren experience. I actually don't want to walk in a store and people like, hi, how are you? I'm yourself. I'm like, what? Like, let me come to you. You know, it's like. And so CHCM is actually like, my personal favorite style of service and everything.
Jake
Yeah.
Eddie
And before then, it was Union on Spring street when Marianne ran it. You know, like, those are my two favorite stores all time, like, in life.
Jake
But did you say earlier on a previous podcast that, like, you also had to kind of, like, become friendly with the people at Union? Yeah.
Eddie
You know what?
Jake
Like, they wouldn't sell you stuff.
Eddie
There was a dude, I think his name was Ricky, used to work at supreme. And, like, he was just like. He just. He was like, you know, I'll give it to him. He had style. He, like, into French khakis early and stuff like that, but he would just, like, check people. And I think this was in a moment where in streetwear and menswear, people didn't want to be associated with urban. And I was just, like, still very Jimmy Jazz. And I like. Like, I still love urban style. You know what I mean? Like, Vinny styles, Jimmy Jazz, shit like that Albie Square Mall. I think that's, like, the essence, you know? I mean, like, I think people are cribbing that still all the time. And so I was just. I was doing that, and then they wouldn't sell me stuff a lot of times. And Wilkins became my homie, and Wilkins would just give me the shit because he'd rock it, and then it'd shrink, and then he'd give it to me. And then Marianne was just really nice. She was the owner, and, like, she just saw me in there all the time, was like, yo, you cool. You cute. Like, you nice. And, like, you know, like, whatever you want, just talk to me. And so Marianne became my homie. And funny enough, little known story outside of, like, the supreme community, but Marianne is also the one that, like, found Aaron Bondaroff when he was working at Whole Foods. And then he became, like, Face of Supreme, mastermind of supreme, and, like, he's another dude like Sweetsu who like I'll fight, I'll fight somebody for a Ron. Cause like a Ron really like just had the vision of a lot of.
Jake
Things, like, you know, yeah, for sure. And also I was like, to what you're saying about chcm, you know, like the employees there, like Rich is a guy who I'll go in and see him and he's like, always looks so cool and all this stuff too. And I'm just like, yeah, like, you know, he's wearing a sweater from like Tiger Takahashi. And I'm like, yeah, that's the one that I'm going to buy now, you know.
Eddie
Yeah, yeah.
Jake
He just looks really, really, really, really cool in it. Oh. To go way back to where we're talking about. So basically I bought a jacket at this Barney's co op in Philly that was like on 50% off or 60% off, whatever it was at the time. And then I liked it so much I was wearing it all the time. Like it was like this cotton zip up hooded windbreaker with this hand embroidered pattern across the chest, like this dobby pattern. And so I saw the label, I thought it was cool. They also made these flannels with like this oxford cloth lining in these flannels. I just thought it was like really cool. And they had this like metal locker loop in them too. I just thought it was like really, really thoughtful and different. And then so I ended up reaching out to the brand. This would have been like March or February or March of 2010 when I was still a freshman in school. And then I just said, hey, like I bought this jacket. I really like it. You know, like, do you guys take summer interns? And then they were like, you know, like, like, kinda like, you know, we're just two guys, but like come up to New York on your spring break and do an interview. And then it's exactly what I did is, you know, went home to Connecticut and then took the train down, did an interview. And then, you know, they were like cool. Like you got it. And then the way that I got hooked in the whole industry was I started interning for Berkman Bros. In June 2010. Literally a week after that, after I started, there was a big trade show in Men's world called Capsule. And they had, you know, New York and Paris and maybe one other place.
Eddie
BPMW put it on. Right? Correct Brand Pimps Media horse.
Jake
Yeah, exactly. Those guys.
Eddie
Legendary.
Jake
Exactly. So Capsule had a Paris trade show. And so the guys, Ben and Doug Berkman were Doing the trade show. And they said, you know, like, we need your help. Like, we're going to Paris. And at the time, they were also talking to this guy who was, like, thinking about investing in them, who had something to do with Moncler. And this was right at the very same time that Pharrell just started a collaboration with Moncler. And so in Paris, they were having a party at Colette. And so basically, I start interning for this company. A week later, I'm in Paris at Colette, and I met Pharrell. And after that, I'm like, well, what else am I going to do? You know what I mean? Like, it was such a mind blowing, fun experience for me to be able to do that. That, you know, we came back to New York and I. And then literally, I got back to school in Philadelphia that fall, and then immediately I applied to transfer to go to parsons, which is where I ultimately went and graduated from. Yeah.
Eddie
Ew.
Jake
Yeah.
Eddie
Yo, Speaking like, I love Pharrell, like, obviously the God.
Jake
Yeah.
Eddie
But I do love the era when people were shading him like, pharrell can't skate. That was one of my favorite fucking streetwear tees, was the pharrell can't skate shit. That shit was hard. Cause that's what I like about downtown New York street world culture was, is like, once you got too big, somebody had to fucking shiv you a little bit.
Jake
Yeah. Yeah.
Eddie
You know, like, that is the cool part. Like, that's when you know you made it when cats are rocking the frill.
Jake
Well, that's like, even what they said in, like, the Michael Jordan air, Ben Affleck, Matt Damon movie. It was like he has the whole speech at the end about, like, here's how it's gonna work, you know, like, you're gonna. Everyone's gonna love you. You're gonna be a God to people, and then you're gonna get to a certain level, and then they're gonna tear you down, and it's like. And the key of, like, true greatness is, like, whether or not you can get torn down after being on the mountaintop. And can you persevere through getting torn down and come out the other side of it? And that's like. I thought that was very true of what you just said about Pharrell as well. Not that he was ever truly torn down, but in terms of, like, a small. Yeah, people.
Eddie
Cats just had to ding him up. Like, you had a little. You had a lot. You had a lot. And now he got even more. And so now it's just like. It's what happens. You pop the crabs in the barrel, try to bring you down just a little bit, and then if you get out the barrel, it's like standing ovation.
Jake
Exactly.
Eddie
Play that Jeezy TM101 standing ovation.
Jake
Exactly like you. That's when, you know, like, you've. You've ascended to, like, Mount Rushmore.
Eddie
Yeah. Cats can't fuck with you. Yeah, that's it.
Jake
Yeah.
Eddie
You know, and that it is. That is like the hero's journey.
Jake
Exactly.
Eddie
The epic story. Beowulf.
Jake
Yeah. Right. Yeah.
Eddie
That's what happens.
Jake
Build you up, get torn back down, and then if you can make it through, then. Then you'll like, really be one of the greats.
Eddie
Yeah. But on some granular New York shit. Because that's what this pod is. On some granular New York shit. You were part of this really hilarious. Hilarious to me.
Jake
Okay.
Eddie
Menswear movement on Tumblr with, like, Isaac likes and Larry and James from Throwing Fits.
Jake
Yeah.
Eddie
I feel like it was kind of before you guys and the. The 316 guys making jeans and like. Yeah, there was just like that. How did that all come about? Cause I like, watch it from the side. Like, yo, Larry, what are you doing?
Jake
You mean like the whole, like.
Eddie
Fuck, yeah. Menswear.
Jake
Yeah. Suited and like, and, you know, just. I mean, I think, like, as I've gotten older and, you know, I've spent time now in, like, other sort of subsets of, like, watch people and car people. And obviously, menswear people is like my, you know, bread and butter. But it's like, I just think I see the Vacheron. Yeah.
Eddie
I see the Maltese cross.
Jake
Shout out.
Eddie
Put it up. Put it up.
Jake
Shout out to Michael Zickert. I'll just come clean. Michael Zicker from Vacheron.
Eddie
You gotta put it up a little harder. Come on.
Jake
Yeah, no, so. So I'll do it with you. This one is still. This one is still owned by Vacheron, but he's just letting me rock it for a couple weeks because I'm just friends with the guy.
Eddie
You gotta say that.
Jake
No, I want to come clean. I want to come give him this watch. Give. Beautiful. It's. It's actually truly. I'll probably make a video about it this week while I have it, but it's just like, if I had 40 grand to drop on a watch, then this would be the one. Like a brand new watch. This is the one that I would get.
Eddie
No, I know the program. I'm up for it too. I'm supposed to be loaned a gold 222 for six months, and I'm just like, I need that. Like. Like, my dick is gonna feel like 75 inches bigger.
Jake
Yeah. This one. This one. This one is beautiful. And I just like, I'm gonna be.
Eddie
Sucking my teeth at myself.
Jake
The gold 222 is. Is. Is amazing.
Eddie
That's my. That's my Excalibur watch. Like, the gold two two two is the hardest. Like, cats are on the steel. Cool, cool, cool, cool, cool. Accessible. But the Gold 222 is just like.
Natasha
You're a gold guy, though.
Eddie
I'm gold.
Natasha
You're a gold guy.
Eddie
Yeah.
Jake
Yeah.
Eddie
And honestly, I'm usually not last name in yellow.
Jake
You know, I'm usually not a gold gold guy, but this is actually pink gold. And I think it's just. It's just beautiful.
Natasha
Yeah, it looks really great on you.
Jake
Thank you. Yeah. It comes in two sizes. 36 millimeter and 40. This is the 36. Because I just like smaller watches, and it just feels a little more old school and classic. But yeah, this is the 1921.
Eddie
Beautiful. Because. Yeah, those don't know. Vacheron don't do solid gold right now. It's all rose.
Jake
Yeah.
Eddie
Unless it's the reissues. Unless it's vintage. They're rose right now, which I think is fly. Like, Vacheron just makes very cool choices. That makes them slightly less accessible, which is why they are my favorite watchmaker.
Jake
Really?
Eddie
Yes, absolutely. Absolutely. Like, you know when your signature is the blue dial, that doesn't go with everything. I'm like. I kind of like that. You're like, standard mode is like, come cop the blue dial.
Jake
Yeah.
Eddie
And it's like a cobalt blue. It's not like navy. It's not, you know, toned down. It. They're just like.
Jake
It's blue, you know? Yeah. Yeah. And my, like, regular daily watch is like a mint green Rolex datejust so, like. That's the one. Yeah. Which is. Yeah. Which is a super simple. But, like, I do like that it's green and not typical because it, like, it doesn't always go with the outfit. But I kind of like that. You know, it's just like the green. The green dial doesn't always just make sense, which is kind of cool. What were we talking about before the watch? Oh, I was saying. I know. What I was saying was about how all these different communities to go back to, like the FM menswear stuff is dudes in every corner are Just nerds, you know? And so, like, it doesn't matter what category. You're just like, I was in Milan with Audi a couple weeks ago, and, you know, they were. It's like, I'm around car people, and it's just dudes sitting around a table talking about their favorite car. Like, oh, you remember this car? You remember this one? And then you get to Natasha, no.
Eddie
Mad about cars.
Natasha
Yeah, cars. But, yeah, guys that are talking about. They're like, the way that the engine sounded in 1968.
Eddie
And I'm like, she knows more about cars and dudes will shade. And I'm like, bro, don't talk to me about cars. She knows cars.
Jake
So, like, you know, like, it's. It's. It's this funny thing of in all these different subsets of just, like, one, one, one upmanship, where, you know, like, you'll. I'll come. I'll be in a conversation. I'll be like, yeah, you know, like, I just love the, like, 94 Audi RS2 Avant. And then, you know, a guy's like, yeah, that one's cool. But what about. What about this one? And then, like, what about this one? And you're like. And you're like, this. Yeah, that one was actually a piece of shit. It's actually. This is the one that I would get if I was getting it. And so, same thing in menswear, you know, So I think there was just a time 15 years ago, which, in hindsight, feels very innocent to a certain degree, because, like, that. I mean, for me personally, it was like high school, you know, coming in on the train to the city to go to, like, the J. Crew liquor store and, like, buy my first pair of red wing boots type stuff. And, like, very, very simple. Like, in hindsight, very, very simple stuff. But just once you got immersed in it, and then you saw there were other dudes out there who were as willing to get as nerdy with you about it, you know, on the Internet, because, like, maybe in your hometown, wherever you were from, like, there wasn't a homie that you had that could, you know, really go that deep into salvage denim or whatever the hell you wanted to talk about. And then so did. Yeah, like, meet people on the Internet who shared that same passion was. Yeah. Sort of what. What bonded us, you know?
Eddie
Yo, that shit was cool to me because I'm just a little bit older than you.
Jake
Yeah.
Eddie
You know, like, and I never got to bond with cats on the Internet, like, as a teenage, you know, like, I mean, I would talk To Shorty's on aim. You know, like, that was the extent.
Jake
Do you remember your screen name?
Eddie
It must have been something. I think I was always Wong. Wong 2434, which was Charles Woodson, Champ Bailey's number and Charles Barkley's number. I think that was always just my.
Jake
Yeah.
Eddie
And then. But no, like, I remember I would like buy Dipset mixtapes and Green Lantern mixtapes off the Internet. And that's kind of the only thing I would cop on the Internet.
Jake
Yeah.
Eddie
And otherwise I had to like go to the reggae store or go to the head shop and cop like the T shirts and magazines. I would read the source and the source was like the window gateway to like culture I wanted to like be a part of and was interested in. So I'd read the source, but like, the source was my Internet. Like, that was it until I came to New York. And then I was like, oh, I could just walk into Union. I could walk into Nord. And I was like, I remember the first time I saw BBC ice cream shoes. I'm like, what is this? And everyone in the store signs, come on. You don't know what ice cream is? I'm from Orlando, Florida, Right. So I had to like get in that way. And I kind of liked that hard knock way of just like getting sunned for years and insisting on like getting into a community kind of.
Jake
Yeah. And I mean, it certainly happened on the Internet too, where there's like that period of like, hey, what do you guys think about my fit? And everyone's like, trash, trash, trash, trash, trash, trash, you know? You know? Yeah, yeah. I mean, that's. That still happens on.
Natasha
That happens today.
Jake
Yeah. On Style Forum guys are still doing that. Like, if I'll have a question about like a product, I'll be like, you know, wondering, how does this like pair of dress boots or whatever it is, like loafers fit? And then you'll go on Style Forum and it'll be like a guy with like a close up of like his like just ankle down and be like, are these shoes too big? You know, like there's. It's still going on on to this day.
Eddie
No, we've been talking about this a lot on the pod where it's like, yo, I love these memories of just getting sunned. It's okay. Like if you out there and you listen to the show, it's okay to be sun. I think everyone's so nervous now because there's like an economy tied to your image and your Instagram and your comments. So you don't want to, like, ever be wrong. You never want to have a trash fit. And I'm like, dog, all of us are trash. No matter how hard we try, we're going to look back in a year and be like, that was trash. That was such a. It's fun to be trash, for sure.
Jake
I went. I just wrote a thing for my substack about, like, how I predict that skinny jeans will come back and how I am now.
Eddie
Saw that. I was so mad. I'm so mad. You said. You said Jacob Elordi is peak baggy pants.
Jake
Yeah.
Eddie
I was like, you'll take this back right now. Yeah, because, like, bro, this. Like, look at, look at.
Jake
Yeah, look at him.
Eddie
Like, bro, this is my normal shit.
Natasha
But you're baggy pants for life. You're like the constant.
Jake
You feel like you found, like, did you ever get on with, like, the, like, the apc, like, new cure?
Eddie
No, I can't even feel fit. I mean, the dumper. The dumper too. Fire.
Natasha
Like, you're the rare person who, like, you. You commit to your baggy pants and, like, you're just riding the wave. And at points you'll be like, it'll be baggy pants and it'll be like, yeah. And then it'll be skinny jeans. But you're still bad.
Jake
Yeah. You have a Ralph Lauren mentality. It's like, it's like, I'm just gonna do me, and then the trends will. Will come come around back to me. Eventually we meet.
Natasha
There's people that are, like, going to do the trends, and there's people. People that are like, you have your silhouette. Your silhouette is baggy pants.
Jake
Yeah.
Natasha
You could, like, change it up on top, but your baggy pant.
Eddie
You. Yeah. And you also, I feel like, is very like Carolyn Kennedy. Like, there's always a bit of. I feel like there's always 25, Carolyn.
Natasha
Private school kid from Massachusetts. So the two wolves inside of me are stripper. And then, like, like, literally boarding school.
Jake
Bad Gilmore girls.
Natasha
Yeah, Gilmore. Like, literally. I'm like, I will have two polos on. And, like, then you'll see me the next day. And it's like sheer nipples out. Like, not even wearing a thong. Like, you're just seeing full back.
Eddie
Like, that's just so hard. I knew she was my wife because I. I used to just, like, hump the couch looking at, like, Ralph Lauren purple ads with shorties on horses. And I was like, so. But, like, I needed. I need a sluttier one.
Natasha
Experiences, like, growing up would be like me and my mom would go shopping of course. Like single mom vibes. Like our, our bonding was like we're gonna go fuck up the mall.
Jake
Yeah.
Natasha
But in her dream for me was to be like this preppy like Ralph Lauren. Like to this day she will like shop for me and send me stuff and it'll be like all Ralph Lauren. And that's her dream.
Jake
And you were like, I want to go to limited to.
Natasha
It like rubbed off and for sure. But I what?
Jake
That's, that's where my sister was.
Natasha
That's why I said limited to. There's the funniest meme and it's, it's the meme and it's this long ass receipt from limited to. It's like the CVS receipt. And it's like this was, this was my receipt from the day after my parents divorced. And I was like, that was my life. That was me. I was up in Limited to. I had like an N initial purse with glitter on it. I had like trouble on my T shirt and like tight, tiny little like rolled over Abercrombie too.
Jake
Had had teen girls in the early aughts in a chokehold.
Natasha
And you know what's so sad for me where who is the limited suit right now for girls?
Jake
I don't know.
Natasha
Yeah, there's no. Like that was so fun to just be able to like experiment with fashion at that age and not be like already trying to buy like I don't.
Eddie
Cats are like I'm a 12 year old creative director. I'm like dog, go eat your own poop.
Natasha
But I see these like young girls and they're wearing blue lemon and it's just not fun fun. I'm like, cool.
Jake
I will say that something like from the pre Internet era where it was like, I just remember, you know, to go back what you say about being like flamed or whatever. Like going to champ sports at the mall, getting like a terrible in hindsight like a terrible pair of sneakers that like I don't even remember what they were called. I just one sticking out of my mind in sixth grade where they were like Timberland boot material but they were a basketball sneaker and they had a, they had a flap that went across the lace. Yeah, laces. And they had a button for like the flap. And then I just remember getting like cooked like in sixth grade for these shoes and like they were bad like in hindsight. But like I had that experience, that very important experience of being like there's no one around me to tell me or there's no, like, website to tell me what sneakers to buy. So I went into Champ Sports and was just like, I like these, and I'm gonna buy them.
Eddie
My most embarrassing clothing moment is also at Champ Sports because my ninth grade year, my mom was like, Here's $100. Go buy clothes for the fall. And I went to Champ Sports, and they had $20 Nike Polos Navy. And I was like, oh, I can get five of them is Monday through Friday. I don't got to worry about shit, you know, like. Because I was like, I just need to have clothes, right? So I copped them. And the two flyest dudes in my school was a dude. Romine, Hamza, Louie, still Dumb Fly, and my other homie, Easy Eric, right? And it was a Dominican homie who was super fly because his father had passed away in the Air Force. So he got a $500 check every week and was just up in Foot Locker going crazy. And I had this. This Nike polo on. I was like, this shit fly, right? And Romin looks at me and goes, dog the Champ Sports logos on the sleeve. And I looked, and it was cheap. It was $20 because it was the employee shirt. I had copped five employee shirts. And he's like, you look like you work at Champs Sports. I was like, fuck.
Jake
Fuck. I love that.
Eddie
The most embarrassing.
Jake
The equivalent of literally buying the referee shirt at Foot Locke.
Eddie
That's what I did. And then my homie, Easy Eric was. Was really cool. Like, he felt so bad. He was like, all right, you could just start wearing my clothes after I rock it the first week. I was like, no doubt. And, like, he gave me all the fly. So I was just styled by this Dominican dude with Air Force money.
Natasha
I love your. That's how your inner child I, like, love. I want to, like, give your childhood self a hug. That's, like, the sweetest thing ever.
Eddie
Oh, I was bodying.
Natasha
But it was just such a cool era. Like, I feel like we're a similar age. And I remember just even down to, like, the choice of your cell phone. Like, things now are so kind of like, you have an iPhone. You have a Samsung. Cool. Keep it moving. But, like, I remember you could have an LG Chocolate.
Jake
I had an LG Chocolate.
Natasha
I had the pink razor, and I had a Sidekick. There was so. And then there was, like. I don't even know. There was so many choices to make even from your cell phone. Like, there was just. So you could be anyone. You could do any. Like, taking a chance and taking a risk. Was like, so different than now. I see, like, young kids coming up and they all have to have the newest iPhone. Like, even my little, like 11 year old niece and nephew will son me and they'll be like, you have an iPhone 16?
Jake
That's like, crazy.
Natasha
You didn't get the new one yet. And I'm like, shut the fuck up.
Eddie
Shut up, you guys. I would say grew up in the greatest era of fashion I've been alive for. Because, like, we had the. The polo Tommy Nautica thing, which was very, very fly. We all love it. But y' all got the like supercharged, like on crack with nitrous, like, version of that.
Jake
Yeah, like, sure.
Eddie
Sean John fat farm apple bottom. Like, y' all juicy. Y' all going crazy.
Jake
Yeah. And now. And that's the stuff that, like, I feel like the. The Gen Z TikTok kids are like, coming back to now, you know, Like.
Eddie
But what's funny now is I'm like, yo, everyone's so into arc. I don't remember as a kid being like, oh, I want my grandpa's clothes. I was never looking back. I was always looking forward.
Jake
Sure.
Eddie
And I'm just like, what. What is. Like, just make some new shit.
Jake
Yeah, for sure.
Natasha
Feel that. For sure.
Jake
Yeah. I always wanted, like, the new. The new cool thing or like, seeing, like, what, you know, like, oh, four college dropout. Kanye was definitely, like, super, you know, like, oh, I'm gonna wear a pink polo or wear the two polos situation, you know, like, always looking to, like, what the actual cool people in the world were doing.
Natasha
Not.
Jake
Not my dad.
Eddie
I feel we're not progressing because cats are too worried about making a mistake.
Jake
Yeah.
Eddie
Like, if you look at Kanye with the, like, like the. The shades.
Jake
Those are in high school.
Eddie
It looks crazy now.
Jake
School dances, everyone had a pair of shutters.
Eddie
You had to do that.
Natasha
You had to do that shit say, too. It's like, I think that era of celebrity, we had so many, like Kanye doing unique, like, Cameron doing unique things. And not to say these people didn't have stylists for things, but, like, they were dressing themselves regularly. So there was a personal style. And even like, like every time Jacob Elordi steps out, I'm like, somebody dressed you like you're at the airport and somebody dressed you like they're just never. I mean, like, I would say Bella Hadid is probably one of the famous, famous people that I know. She, like, famously, like, styles herself. So when you step out, you're like, okay, I'm getting a piece of personal style. But like, so many people, I'm like, everyone is just so styled all the time.
Eddie
They're wearing the same clothes.
Natasha
And you can see. I'm like, sure, I can see the reference. I can see it. And I'm not the most, like, fashionable person, but even I'm just like, I would like to see somebody do something, take a risk, and, like, be moving forward and progressive. Do you think that there's anybody that, like, that you have seen that you're like, that person's doing that?
Jake
Well, I think I was. As you were talking, I was thinking of Matty Matheson because famously doesn't have a stylist. And, you know, but he looks so, so cool all the time. You know, Like, I forget which awards show it was, but he showed up in a tuxedo doing award show a few seasons ago, and I was like, out of every single person here, no matter which celebrity they are, he is the best dressed person here. And because there is a sense with Matty of, like, authenticity, of like, I don't need a stylist. I'm just gonna dress myself.
Eddie
Yeah, Matty's always been him.
Jake
Yeah.
Eddie
You know, he definitely looked like he could be on a bottle of pancake syrup. Like, that's his thing. Like swan. Yay, pancake syrup pitch man. That's how I see him. And he always. He always been fly.
Jake
Yeah, he, like, looks really, really cool. And. And, you know, you can tell because, like, I do think Jacob Elordi looks great in the clothes that he wears, but he's 6 foot 5, very handsome guy, like, looks. He's just. He could literally wear a trash bag and, like, look cool in it. And then so when you, you know, when you see someone who does have a very strong sense of personal style out in the world buying their own clothes and. And also think it's not just like, it's like, Jacob looks so good, but do I believe that, like, he is going to, like, Venspace or CHCM himself to buy this stuff? Like, I don't. I don't buy it, you know, like.
Eddie
Also, Venn space is like chcm's son. You know what I mean? Like, they're definitely.
Natasha
If they got a coffee shop and like a fucking wooden bench or some shit, you know?
Eddie
Yeah, I like, want to go to venspace because I've seen the images.
Jake
Yeah.
Eddie
But then I saw, like, so many brands of Venspace are already carried. Buy suiteu at chcm. I have barred myself from going to.
Jake
Venspace, But I'll say, you know, like, I've known Chris for a while who owns Venspace, and it's a very, very lovely store. And there are some different things, you know, like, I mean, they both carry orally, for example, but, like, you know, Chris has this. This brand, a press out of Japan that's very popular, but, like, Sweet Too doesn't have it. Suite two carries Evan Kanori. Venspace doesn't. You know, like, there's certain things.
Eddie
They got Teotoro at Venspace.
Jake
I don't know. I actually don't know Teotoro.
Eddie
Is that okay? Like, Sweets who really put me on a Teotoro. But respect. Respect.
Jake
Yeah.
Eddie
Sweet Too allows me to go visit Venspace. I will peep.
Jake
Yeah, just go to. Go to CHM first. Be like, hey, I'm thinking about going to Vent Space and just see what he says.
Eddie
Yeah, I will. Space guy don't carry what Suey 2's carrying. Find something else, because he already found it.
Jake
Yeah, he got it. So they. They. They do have, like, kind of, like, kind of different. Different things.
Eddie
I'm curious. I'll say I'm curious.
Jake
Yeah, you're Venn space curious.
Eddie
I'm Venn space curious.
Jake
Yeah.
Eddie
Absolutely.
Jake
Yeah. And so, like, I guess to go back is just, like, there are a lot of celebrities out there who, by virtue of either having stylists and also just, like, in some ways, is very positive. The democratization of fashion information. It's maybe a little bit easier nowadays for a celebrity to be like, oh, that's the. That's a B. A plus B plus C equals good fit. And, like, because I saw it on the Internet and, like, I'm just gonna do that.
Eddie
Like, I will say we. We've been talking menswear, but a woman with, like, cool personal style, to me, is like, Chloe Cherry. I think Chloe Cherry has, like, a cool personal style. Like, it's not my style, but it's like that. It's. It fits her.
Jake
Right.
Eddie
You know what I mean? Like, I like when someone's style feels like an expression of what's actually inside. And. And I would say that Maddie is like that.
Jake
Yeah.
Eddie
You know, Like, I think Maddie's style is who he is.
Jake
Yeah.
Eddie
You know?
Jake
Yeah, for sure. And so to go back to your point, like, I just think, like, it is. There's. There's probably been no. No other time in history where there have been more good fits in the world. But, like, good fits aren't necessarily, like, the highest level that you can achieve. It's like, it's like, it's gotta be good and, like, different and cool and personal to that person.
Eddie
There's a lot of correct answer fits.
Natasha
Yeah, it's correct answer fits because I will say, when we look back and everybod pulls a reference of, like, the best fit from this award show 20 years ago, at the time, that person was getting fudgeing, roasted, and they were like, you look like shit. And now we're like, no, that was the one. So I do think the correct answer fit is just a little.
Jake
And I think that's why, like, the mood board culture is so, so big, because, like, you go back to, you know, any. Any sort of event happening in Los Angeles between the years 1985 and 2000, and just go to the Getty Images and just see what people were wearing, and you're like, you know, I don't think when Bruce Willis was married to Demi Moore and, you know, he was wearing big pleated Armani shorts that, like, anyone gave those to him. He just was like, oh, these are cool. Big pleated shorts, and he looked awesome in them, you know? Yeah.
Eddie
And I think there's a funny thing, too, of dudes dressing for dudes. Like, streetwear dudes. It was definitely.
Jake
Which we definitely do in the menswear community. Yeah.
Eddie
Yeah. But, like, from your pov, babe, who are, like, men that, like, you like their style.
Natasha
Men that. I really like their style. I mean, like, currently, I. I really like Tyler, the creator, because I like a preppier kind of vibe. And I think he does, like, preppy with a very authentic. Stays true to who he is. I like that him and Maddie both.
Eddie
Have a cheeky thing going on.
Natasha
Yeah. And I, like. I just think I'm like, he always looks like he was just wearing that when he goes somewhere. Do you know what I mean?
Jake
But also very put together. Like, very thoughtful about this thing with this thing.
Natasha
Yeah, it's intentional. But I'm like, he didn't, like, buy this outfit for this thing. Like, he would have just been at dinner, but he's here. We're. I'm like, you look like playing chess on large, which is what I think is the most. Whenever I see style out in, like, the street, and it just. Even when I'm on, like, the Upper east side and there's a woman and she's just get. I'm like, but you look, to me, the best fits. I'm like that. You just look like you're living your life. You would have been wearing that regardless. I don't think when I see them, I'm like, you didn't get dressed to impress somebody today or like, get a fit off. You were just wearing that. And I like that. But I think Tyler, I think, think.
Jake
And Tyler also, that. That carries over to all of his taste, you know, whether it's like his watches, where he cars. He has the most amazing cars, like Launcher, Delta Integrale, Evo.
Natasha
The same birthday.
Jake
So you and Tyler do. Yeah.
Natasha
March 6th, Pisces.
Jake
That's not you, right? Because you're March 1st. March 1st, me, Justin Bieber.
Eddie
You know, that's my energy.
Jake
Tupac.
Eddie
I see it.
Jake
I see it exactly. June 16th. Yeah. Yeah.
Natasha
I will say. God. I'm like, I don't really pay attention to men that much.
Jake
Good.
Natasha
I like Tyler. I think all athletes right now in the over styled era, just. I can't do it with like the fit picks and whatever.
Jake
Like, I do think Shay is cool, though. Shay Gilgis Alexander, he.
Natasha
I don't know who that is.
Eddie
A little too shiny. It's like, it's a little.
Jake
I think the whole package with his outlandish fits and the captions. The IG captions are amazing.
Eddie
It's fun. Yeah. You know what, though? It's. It's performed like. Nah, you know what? I'm just gonna say, I'm not buying. Like. Like, he's. It's AI. Like, AI. It was like, that's just him. Like, that's just him, bro. And like with Shea, I'm just like, yo, it's too shiny. It's placed. All of it's placed.
Jake
Maybe I. Maybe I. I bought into the. The Shea propaganda style propaganda. Yeah.
Eddie
I like when they put the jerseys on the reporters at the end of the game when, like, Jay, it's.
Jake
It's the whole. Okay, see, it's a whole team.
Eddie
They put jerseys and put on to whoever's interviewing Shay. I love that part. But like, n. He's. He's. He's putting it on. And like, who else? What were you going to say, baby?
Jake
Oh, sorry.
Eddie
Something.
Natasha
Oh, no, I was just saying I like, don't even think athletes. I pay attention to men. Yeah. I think athletes like you saying, like, Alan Iverson used to have incredible personal style. Like, I would even say, like, Dennis Rodman. Like, that was crazy to me to be a kid. I was like, what the fuck is that? I didn't even know you could do that. Like, I didn't even know there was choices like that out there. That was just incredible to me. But now I feel. Yeah. I'm just like, when they show up to the. I'm like, you're styled like, somebody put this on you. And that's not bad. That's not a bad thing. But I'm just not drawn to any of it.
Eddie
Like, I'll say, Cameron Brink, beautiful person, great fits, correct outfits. But you can just feel like in her mind, she's like, I'm doing it. And I'm like, I don't want to feel like you're aware you're doing it.
Jake
Yeah.
Eddie
I want to feel like you're going to buy milk.
Jake
Yeah. Yeah.
Eddie
I think is kind of what you.
Jake
Show up to the stand.
Eddie
We've seen Tyler in fits like every. Like, on Larchmont. You'll see Tyler playing chess out there, and he's just look fly in his element and he don't want nobody to watch him play chess. He's playing chess.
Jake
Yeah. Yeah. And you know, and I think also with, you know, to go back to AI, like, and meaning Allen Iverson, not artificial intelligence, to go back to him. Like, that's why I was so influential, too. Like, you know, like, there was, you know, kids up in Newtown, Connecticut, wearing finger bands to play basketball because of Allen Iverson, you know, And I don't know, like, today, if there is that athlete who is, like, inspiring the way that people dress to that same degree, whether it's their daily lives or on the court or whatever. I don't know. Maybe there is.
Natasha
But who do you think is inspiring men how to dress right now? Like, who do you think is the main kind of like, male muse for men who dress for other men?
Jake
I would say there's a trifecta that comes to mind of Elordi, Austin Butler and Jeremy Allen White.
Natasha
Okay.
Jake
That's like the.
Natasha
That's so. Yeah, those.
Jake
Those three seem to be, like, the most tick tockable.
Natasha
Okay. I. I think. But the OG was Shia LaBeouf.
Jake
Yes. I mean, he's. He's. I mean, he is. He is the source.
Natasha
Yeah. I'm like, I don't even know. I just.
Eddie
Not his personal. But the. The thing in the style when we.
Natasha
Were just getting, like, fit picks, I just remember, like, a span of four years was like, everything. This was just like. I was like, I don't know, you.
Eddie
Know, Kanye dug his class.
Natasha
Yes.
Eddie
So Kanye went through his fucking.
Jake
So one of my. So I had like a real. One of my. Like. True. This is so silly because, like, I'm like a blogger, you know, so, like, I didn't do even when I Worked at gq. I wasn't doing a whole lot of, like, reporting reporting. It was more just like, I'm gonna tell you about this new shoe and what. Whatever. But, like, one of the, like, the. The, like, proudest career moments of mine was when, you know, I was following Shia and Kanye's fits religiously. Like, there was like a whole Twitter joke for years that was like, Shia LaBeouf fit watch, you know, and you just like, whatever fit he was wearing, you just tweet out a picture with that. And like, there was a whole Instagram account that called Shia's fits at a certain time. And I remember. So I saw Shia, he had done this movie Fury, and so he was wearing this, like, tank school hat. And then, like, two years go by, and then I see a picture of. Of Kanye walking out of his office in cargo camo, cargoes yeezy 700s, a comme des garcons archive sweater, and this tank school hat. And I was like. I was like, oh, I think shy. That's the same hat as Shia. And then I was, like, looking at it closer, and I was like, Shia's had signatures all over it from the cast of that movie. And I was like, I think that's the same fucking hat. Like, the exact one. And so I like, whatever, whatever. And then figured it out, and it turned out it actually literally was like, Shia had given Kanye his exact hat off of this.
Natasha
Did you break this?
Jake
Well, the funny part was, I guess I did break it, but then afterwards, I tweeted out about it, like, with my theory. And then Kim Kardashian was like, yes, it is. Like, she retweeted me, was like, yes, it is Shia's hat. It's Kanye's favorite hat.
Natasha
How you broke this. So I was like, hard hitting fashion news.
Jake
Exactly. At the time, it was like, for me, it was like, oh, I'm actually like a real reporter now.
Eddie
Yeah, no, like, I didn't read it, but he was in the gym one day and told me about the shit, and I was just like, okay, yo, Kanye went through your closet like that. And so, like, yeah, he's. He's ill. I will say this too, about Shay. Shay Jill, just because, like, I couldn't answer in the moment. Exactly. But it was like, it's places shiny. I'll say that his style reminds me of one of my former best friends, Will Perkins. He's like a creative director at Supreme. So I've seen someone do that style, and it was real. And that was his closet. And he just Throw it together. Chain link necklace, locked out glasses, you know, a shirt, leather jacket, motorcycle jacket. And it just never felt like plate. It felt lived in when my homie Will would do it. So when I see Shy do it, Shay do it, I'm just like, I seen this and you not. That's not your life. Yeah, that's how I feel.
Jake
You think that he's not. If he was going to whatever the Oklahoma City equivalent of Erewhon would be like, he's. When he's going there, he's not wearing anything even remotely close.
Eddie
Yeah, because I know the dude that used to live in Silver Lake and get on a motorcycle and drive to Erewhon in that fit because he needed that fit to get on his motorcycle.
Jake
Right.
Eddie
So I'm like, when you show up at an NBA press conference wearing it, this doesn't make sense.
Jake
Well, I just think in general we're talking about is just like modern celebrity being so, you know, tapped in. Like, everyone's got like their, you know, Jacob, Lordy has like a Bottega sponsorship. You know, it's like everyone has. Every athlete has, like, their alignments, you know, so there's just like, it's all part of some bigger, like, I got to do this thing to get this bag over here and then this thing to get this bag over here as opposed to just like getting up and being like, I just think that this looks cool today. It's like all part of some grand.
Natasha
Somebody on the team marketing plan is at inception of, like, the new. Whoever the young Austin Butler is, is like, we're going to put you in this and this and this. And then we're going to align you with Saint Laurent. And then you're going to get. And you're going to be doing this. And it's like, yeah, there's a whole formula behind it. And like, like, you're saying you can tell when somebody. There's an essence that comes out in something that either lets everybody know that you're being authentic or lets everybody know that you're not being authentic. It's just. It's in the ether. You can feel it. I even. Sometimes I get dressed and I'm like, this is. I just subconsciously I saw somebody wearing this on Instagram or something and I thought it looked good. And now I'm wearing it. It is like, not me at all. And I feel like a loser. And then I'm like, I need to get off the Internet a little bit for the next, like, couple weeks because I'm getting too Influenced. And I think even when I walk outside, we'll say this all the time. I saw some girl like. Like, it was like 2pm she was wearing stilettos out, like, just like walking around. And I was like, more of that, please. She's just wearing that. That's her whole thing. She looks great. She looks great. Sometimes you walk outside and you see somebody and I'm like, I know your whole algorithm.
Eddie
I know one of our favorite shoes. We went to go eat at Reservoir one day because I needed to watch the Commander's Game and she needed buffalo wings. And the server pulled up and all she had was a tank top. She looked like she did not sleep for three days in, like, a terrible pair of jeans. But she had a crazy bust down. Like the craziest, craziest bust down. And we're like, yo, sugar daddy definitely blessed her with. And I was like, that's the illest fit. This is so ill to be serving at Reservoir. Tank top, terrible jeans and just bust down.
Natasha
Also crazy. I was like, concerned for her safety. I was like, why are you. I was like, these people in here are gonna jump you or something. And I loved her. And I was like, on top. I was like, I just want you to be safe. I was like, don't get. Don't walk out of this place alone at night with your bus down on. Because it was. Diamonds were dancing diamonds. It was not a fake. There was not a fake, like, diamond on that watch.
Jake
That's amazing. I love that.
Eddie
And I just like, like that. I'm like, that's part of your life. Because this don't make sense.
Jake
Yeah, yeah, yeah, yeah. And. And like, you know, I'm not going to be holier than that. Like, I, you know, I track down the Red Wing boots that Austin Butler wears, like, because he may. He did a whole GQ essentials with them. And I. But I was like, what are these boots? And I ended up finding them. And I bought a pair on ebay because I was like, those are just good boots.
Eddie
But it's cool though, because you're like, in an academic space. You're like an ivory tower space in a good way about fashion.
Jake
Yeah.
Eddie
You know, I mean, like your archive. Like, you're collecting information. Like, it's good that somebody's doing this.
Natasha
I also do that. But I feel like those Red Wing boots are probably very authentic to your personal style. And you've taken time to develop your personal style and it show and like, you're authentic. And when you're wearing something, it's it builds into what you already have. I think what we're speaking to is somebody who, like, goes on Instagram and then is like, oh, cool, what's a Zara reference number for the pants and the shirt? And then you put that on. And I think that's where the inauthenticity comes from.
Jake
Well, even. Even to my example, like, I literally was at Apollo Bagels a few months ago, and there was, like, a guy standing out there who had. I knew. I knew the Red Wing boots. Cause they were exact ones I had. But then he had paired them with the vintage 501s, the French tour jacket, and the exact Sturgis motorcycle trucker hat that Austin Butler wears, too. Like, head to toe, boom, boom, boom, boom. And. And I know it's like, it's. It's one of those things where it's like, I know 99.9% of people have no idea what you're doing, but I know what you're doing.
Natasha
And I was.
Jake
And I was like, damn. Like, it's cooked. Yeah. Yeah. Cooked, bro.
Eddie
And this is the thing, too, is like, there's a funny thing to me, it's like. And you're kind of in the industry, and I read all your stuff, you know, And I read it just to, like, know what's going on. But it's funny, when I see, like, the girls or the guys doing reels, like, check out my fit. You could copy here. I'm like, I don't want it if you wore it. I don't know. Am I weird?
Natasha
No, no, I think. But, like, here also, I, like, get it, and I respect that. And that's a lane, and that's, like, a career on the Internet. And I don't dislike it for everybody else. And I don't, like, say it to critique other people and be like, you're bad for doing that. Like, that's cool. It's cool that everybody like the democracy democratization of fashion, where, like, everybody can look cool and know what to get and feel cool. But, yeah, I think I just, like, really enjoy, because I don't even feel like. I mean, I wear, like, a white tank top with a pair of jeans every day. Like, I don't, like. I'm not, like, into fashion in that way, but I really like going outside and seeing people in New York City, like, just doing unique and interesting shit and, like, not doing the Austin Butler cosplay and Apollo bagels, you know?
Jake
Like, you know, Like, I think that's what's so great about New York too, though, you know, like, is just that you can see in real time trends happening, you know?
Natasha
Yeah.
Jake
Like right now, it's like a couple, two years ago, two summers ago, like, Dries Van Noten came out with these sneakers, like, these very low profile, like, 1970s inspired sneakers. And, like, people on my Instagram feed started wearing them or whatever. But, like, in the two years since then, now it's like I saw a girl in the West Village walking down the street in like, the red pair with, like, her. Her Peter Millar boyfriend. You know, you kind of remind me.
Eddie
Of Peter a little bit. I've always, I've always. Peter. I've always felt that in the best way because I love him in the movie. Do you. Do you get that sometimes?
Jake
Wait, I was talking about the brand Peter Millar.
Eddie
Oh, I was talking about the Hunger Games. He got a little Peter.
Jake
Okay, thank you. No, I was saying, yes, like, like the brand, the golf brand.
Eddie
Peter gets the shorty PETA.
Natasha
Yeah, that's why I was like, why are you saying pdar?
Jake
Yeah.
Eddie
Isn't that his name in the film? You have your. Your energy. Has always reminded me of Peter.
Natasha
Josh Hutchinson. Right?
Eddie
Yeah.
Natasha
Is his name.
Eddie
You're talking about my bad people. It's not always nice to say. I don't know. I think I meant it in a good way.
Jake
No, it's totally all good.
Eddie
I try to be nice now.
Jake
Well, I was gonna say thank you for reading my writing because literally, I mean it, there was a time period when I. I started, like, writing just for myself, stuff on Tumblr in like 2011 or 12, it might have been. And I think it was like, I wrote about maybe like the Channel Orange album or something like that. I just wrote a review for myself or whatever right when it came out and I sent it to you and you read it. And to this day I think about what you said back to me because you were like, you have a lot of good thoughts here, but just structure wise, he's like, just keep it simple. You were like five paragraphs intro, three paragraphs conclusion. Because you were like, you're kind of getting lost in the weeds here and you didn't really land the plane. So, like, just think about that way. And so, like, if ever I'm writing like a longer form, thing like that always comes back to me about, like, Eddie's advice about, like, keeping it simple. Yeah. Yeah.
Eddie
I'm glad it was helpful, man. I really.
Jake
But it was also just really nice of you to like, for me, as a 21 year old kid who just like, was like, didn't really have a real job yet just to like send you something and like, you actually read it and like gave me feedback on. So that was very, like, important to me.
Eddie
Thanks, bro. Yeah, no, it means a lot because, like, I. I really do read like every email, I read every dm and if I, I can help, if I feel like I can actually be helpful, yeah, I'll help. Because you, I mean, bro, I still. I've been reading your writing since and it's just cool to watch people grow and do ill. And like, really. I was looking at the Jacob Elordi Argle. I probably read it over three times. I was like, man, is Maggie fucked again? But then like Natasha said, it doesn't matter. Like, this is just who I am.
Jake
Yeah, you know, it's cool.
Eddie
But your writings, your writing's ill, man. It was. I just gave you that like 3.5 essay genre format because I was like, if you can just commit to structure, then it gives a stage for personal opinion and personal style. Cause if you anchor yourself in a structure, then you can get freaky.
Jake
For sure. For sure. And it's like, still to this day, it's like, I'll find myself in that situation where I don't know if this happens to you, but you write 80% of it. And then you're like, okay, where am I right now? I'm sort of like, I feel like I'm underneath all of these ideas and all these thoughts. How do I get out and how do I come back to the surface and finish this whole thing? And so I just like, all right, like, go back to basics. Here was my intro. Here are the three points that I was making. And now here's what I'm ultimately trying to say at the end.
Eddie
Yeah, I'll end here because this has been awesome. But Chris, Chris has a heart out. And. But I will say this the way I write sometimes, if, like the hand of God is touching me, it's just all the way front to back. And I just publish most of the time. I got to write it, copy it, paste it into another document, and then rewrite it. And then cross check and be like, any good thoughts here? No. Boom. The second one goes. But I usually write every article twice before it goes.
Jake
I feel like for me too, it's a similar, similar thing where it's like, get all the ideas out at once. And then I feel like I now I have maybe it's a little bit different because I feel like I have sort of like a marble slab now of, like, this is, like, a good material here, a good base to work from. And now I gotta go chisel it. You gotta structure. Yeah.
Eddie
There's a format. It's. It' smart. So congrats, dog. Hey, like, seriously, been watching you for 10 years, writing. Congrats.
Jake
Thank you. Thank you both.
Natasha
Thanks for coming on.
Jake
Appreciate it.
Eddie
Awesome, brother.
Podcast: Canal Street Dreams
Date: September 26, 2025
Hosts: Eddie Huang & Natashia Perrotti
Guest: Jake Woolf
This freewheeling episode of Canal Street Dreams features Eddie and Natashia sitting down with fashion writer/editor Jake Woolf for an unfiltered, nostalgic, and highly detailed conversation about fashion, personal style, the evolution of men’s and women’s wear, and the creative ecosystems of downtown New York. The trio shares stories from their childhood and early fashion adventures, discusses the significance of New York retail legends, debates authenticity versus curation in celebrity style, and gets candid about the internet’s role in shaping personal aesthetics. Expect vintage references, playful banter, and sharp cultural commentary.
(00:00–12:30)
Memorable Moment:
Natashia, on discovering her sexuality via Aaron Hernandez:
“I think I like dick. I think I like men. ... Aaron Hernandez turned her out. ... It was a sexual awakening.” (02:45–02:59)
Eddie on new sneakers:
“I used to think I had, like, super abilities with the new shoes. Like, I would read the specs, like, oh, I'm gonna be ill this year.” (07:20)
(11:55–18:30)
(18:30–23:00)
(22:37–26:10)
(26:10–32:00)
Natashia on Limited Too:
“Like, that was so fun to just be able to like experiment with fashion at that age and not be like already trying to buy ... I don't know, cats are like I'm a 12 year old creative director. I'm like dog, go eat your own poop.” (32:45)
(32:55–38:00)
(36:02–42:23)
Jake on Gen Z copying Y2K:
“Now ... Gen Z TikTok kids are like, coming back to [Sean John, Fat Farm, Apple Bottoms, Juicy], you know.” (36:28)
(42:23–52:30)
“Famously doesn’t have a stylist ... but he looks so, so cool all the time ... there is a sense with Matty of authenticity ...” (38:17–38:44)
“I don't want to feel like you're aware you're doing it. I want to feel like you're going to buy milk.” (46:15)
“There's an essence that comes out in something that either lets everybody know that you're being authentic or ... not. ... It's in the ether. You can feel it.” (51:05)
(52:30–59:57)
“I get it, and I respect that ... but I really like going outside ... and seeing people in New York City ... not doing the Austin Butler cosplay in Apollo bagels.” (54:53)
“If you can just commit to structure, then it gives a stage for personal opinion and personal style. ... You can get freaky.” (58:25)
Heartfelt closing:
Jake thanks Eddie for early encouragement and advice about structure, remembering how formative it was to receive feedback and support from someone established.
A vibrant, layered discussion for anyone fascinated by the self-expression and identity wars of fashion, the rituals of becoming, the changing nature of style tribes, and the endless New York hustle to carve out something real. You’ll walk away nostalgic, inspired, and eager to rep your own unique fit—mistakes and all.