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- [00:00]
Sean
If you're a young man in your 20s and 30s, and you want to be more confident, this episode is for you. And it's going to be a little strange. If you saw this headline, if you saw this title, you're going to think, why on earth is this happening on a business podcast? Today's episode is with Die Workwear. Die Work Wear is the username of a person who's gone incredibly viral on Twitter. He has over a million followers, and he talks about men's fashion. I saw this guy pop up last year, and it kind of changed my life because he taught me about dress and how dressing a certain way, it gives a huge amount of confidence. And the problem is that you don't try to dress nice because you don't really know the rules. And so I thought it'd be fun to talk to Derek about his rise, so how he got huge and built a business, but also some practical tips on how to dress better and what that means for your life and what that means for your confidence. So give this episode a listen, and I'll talk to you in a little bit.
- [00:51]
Derek
I feel like I could rule the world. I know I could be what I want to. I put my all in it like, days off on a road less true.
- [00:59]
Sean
I think the reason why you're blowing up right now, I'll give you my opinion, and maybe you could give me your opinion, but I care how I look, and I've always cared about that, but I never really knew the rules. And basically, when you don't know the rules of something, you feel not confident, and you kind of just revert back to, like, well, I'm just going to do the lazy thing of, like, wearing athleisure or, like, kind of boring clothes. But you have this line that you repeat constantly, which is, clothing is a social language, and you kind of have taught people how to speak it, which kind of gives confidence, and it makes your clothing feel like armor. But also, you're dressing like the person you want to be, and you're speaking the language of the people who you want to speak with and kind of what you want to behave like. And I think this is why millions of men have liked you, because you're giving them confidence and teaching them the language.
- [01:45]
Derek
I do think of clothing as social language, and I've always thought of it in that sense, because, you know, if you grew up anytime before the Internet, you know, you may have been part of some social group around a hobby or an interest, like you were a skater or you're into punk music or whatever. And everyone I knew dressed a certain way to communicate an identity, like they were a jock or they were a nerd or whatever. And there was always rules around that look. Even if no one wrote a book and spelled it out for you, you kind of knew that this was the look. And everyone kind of conformed to the look of their social group and identity, and it kind of broadcasted a message. And I think over time, I've just kind of taken that idea and talked about how it's also used in classic tailoring or, you know, techwear or whatever's the aesthetic genre. People are using dress to communicate something. And even people who dress in ways that is subconscious, that they. They think they don't care about clothes, they still kind of dress according to their socioeconomic class. I bring up this example often. There was a moment in the tech industry in the early 2000s where the hoodies and jeans uniform was a way to signal I don't care about clothes. I'm like the whiz kid, you know, kind of hacker that's reshaping the economy. All I care is about meritocracy and skills. But it just so happens that over time, within that industry, everyone started to also dress the same. So to some degree, people are at least conscious of what is the look within their group, and they were careful to not deviate too far from it because they want to signal that they belong. There's a. There's an article that I often mention on Twitter and sometimes in interviews. The author's name is Carlos, but I can't remember his last name. But he wrote an article called Inside the Mirror. Tocracy Mirror, Like Looking into the Mirror and Autocracy. And his article was about how even in the tech industry, where people say they don't care about clothes, everyone mirrors each other. And clothes do play a part. Because if you showed up to a job interview for the tech industry and you wore a three piece suit, people assume that you don't fit in and they will read something into your clothes. So to some degree, clothes do matter.
- [03:58]
Luis
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- [04:30]
Sean
This is the first time we've ever done an anonymous podcast, and I want to ask you a bit about your rise, so if there's ever anything that you just don't want to answer, just let me know. But is this your full time gig now, which is kind of being a writer or whatever it is you describe yourself as?
- [04:46]
Derek
Yeah, I make my living off writing about menswear.
- [04:50]
Sean
There's this concept that I think I learned from you, or a rabbit hole you set me down. Is it called sprezzatura, where it's like you're being careless, but that's kind of the cool part, right? It's like not trying too hard, but you look amazing. Did they explain that accurately?
- [05:06]
Derek
Yes. It was originally introduced by an Italian writer during the 16th, 17th century. And the writer who originally used this term was describing how to serve the king. And they were saying that you should do things in a way that conceals your effort. An easy way to understand this is like if Sam asked me to do a favor, can you pick up my car from this location and drive it to this place? I will do the favor, but insist that it's no big deal, it's not a problem, don't worry about it. Even if it is actually kind of inconvenient. And it's a way to essentially, I guess, serve you is to make the person feel good about what they've asked of you. But Sprezatura, in a men's style sense is basically to dress in a way that conceals the effort that you've put in. But the concept goes way back before this writer. It goes back to even Brummell, who is largely understood to have shaped much of modern men's style. And Brummell used to spend hours tying his cravat, his white cravat, which is kind of like a neckerchief. There's a famous story, probably made up, but the story is that one of his valets was seen exiting the room once with a huge pile of cravats. And someone asked him what? And he said, these are our failures. And the idea was that Brummel actually spent hours and hours and hours in the morning putting together his look. And then he'd walk out and then pretend that he just happened to have fell into these clothes like it was no big deal. It was a complete natural thing. He. He Woke up like this. And that is part of the idea that style is kind of a natural extension of you, and it's not an artifice.
- [06:54]
Sean
And that's sort of. You're doing esprezzatura with your Twitter handle and with your writing and with your reach. You're like, oh, I just kind of just wrote what came interesting. And I don't know how big it is, but in reality, you're just behind the scenes just scheming. You're just. Yeah, you're like, oh, I just wrote this. This really funny burn to this guy who replied. And it just happened to get 2 million views. Because that's what one of your. The things that you do, which is pretty funny is. You, like, reply to a couple people, but you murder them. Like, it's called murdered with words. You just kind of annihilate them. And that's kind of your style, which I find hilar hilarious. But one person you've turned me on to is Ralph Lauren. And Ralph Lauren has an interesting story, but I'm, like, getting obsessed with some of his quotes because he was raised a very normal background. But he said that he got obsessed with movies at a young age. He was like, I, you know, I'm not sure if I can be an actor, but I can design my life via clothing. You know, if I put on a farmer's outfit, I'll feel like a farmer. If I put on a soldier style office, I'm going to feel like a soldier. I'll feel tough and brave. And he has this great quote. He says, I don't design clothes, I design dreams. And then he dresses as. As if whatever he wants to become. He was a Jewish kid from the Bronx. He was like, I want to feel like this, like, old money sophistication. So he started dressing like that and he became it. And I think that's what is interesting about what you've opened up to a lot of people is this idea of, like, acting as if. And then you become.
- [08:22]
Derek
Yeah, if you go through a Ralph Lauren flagship, it's not true for the normal stores. The normal stores are just normal stores. But if you visit a Ralph Lauren flagship, it's like walking through, like, Epcot center, like the amusement parks, and there's like, the pirate ship world, and there's the rocket ship world and all that. You go through a Ralph Lauren flagship, there's like, the ranch world, there's the old money world. There's, you know, there's all these different worlds that he creates around costumes. And it's because he knows how to imbue you with both that fantasy and to kind of use that language and design to reference different social ideas and identities.
- [08:55]
Sean
I want to ask you practical tips on, like, dress and things like that, but I actually want to ask you practical tips first on learning. I've noticed that you're pretty insane. Like, I read a blog where it starts off, like, saying, in the 1959 book Try for Elegance, which centers around men's clothing, and then you, like, quote the book and you tell a story about the book, and that leads into the rest of your writing. I went and tried to find that book that was a book that's out of print, that's like $300 or something like that, and it has, like, no reviews on Amazon. And then you'll do, like, the History of Tweed. And I'm like, how the hell do you know this shit? And so what I want to know is, how are you learning all these things and storing the knowledge? That's what fascinates me about you is, like, your mastery of a topic that.
- [09:42]
Derek
Comes with a lot of buying stuff that ends up being crappy. So I've bought a lot of books on clothing if they're, you know, especially old books, and if it was published in some, you know, sometime, and it was this obscure book, I'd buy and then read it, and a lot of that stuff ends up being crappy. But sometimes there's, like, a nugget. Over time, I think you get a better sense of, like, which books to buy. Obviously, you're not just constantly doing the scattershot. But I do end up buying a lot of books and then reading them. And then sometimes there's like, a nugget here and there. It does help. I would say that fashion as a topic for a while was not treated seriously. And then to the degree it is treated seriously, it's often focused on women's clothing. And then to the degree that men's clothing is taken seriously. There are many brilliant academic writers who focus on men's clothing, but they tend to be extremely academic. So I am in a space where I'm just enthusiast, and I try to write something that ties clothing into other parts of culture, which I hope makes it more interesting to everyday people. And I try to do something that's a little bit smarter than just, like, basic trend reporting or fashion writing, but is a little bit more accessible than academic writing. And then I also tread this water where not a lot of people are treading, and I think that kind of helps. I think it helps to be in this very specific space.
- [11:05]
Sean
Today you had a thing about, like, the quarter zip, and like, that caused so much, so much outrage. And I think I said you were coming on. I got so many people that are pissed off that you were coming because they were like, dude, he's so unrelatable to the middle America guy. And I think, though, that oddly, those people are folks that are being turned on to you right now. What are the common issues that they come to you with, and what's the general advice to the three most common things for, like, if you do this, this, and this, you're going to be 60% of the way there or significantly better.
- [11:38]
Derek
You can't answer any of those things without first thinking of close as social language and the thinking of what you want to communicate. So if you think of clothes as social language, you are to me, like, 90% of the way there, because then you can think of how something should fit and the colors and the styles and all that to combine. I admit that as my account has grown, I've leaned a little bit more towards tailoring. Before my account started grow, I talked about a much wider range of styles, often like Japanese workwear or something. And I've leaned a little bit more into tailoring because that's an aesthetic language that I think more people understand.
- [12:08]
Sean
Is that limited to suits?
- [12:10]
Derek
Suits, sport coats, anything that would be considered, like, maybe smart casuals? I think there are certain kind of aesthetics that, like, everyone recognizes. Oh, that, that's good. Again, bringing it back to language. If you think of, like, dialects, received pronunciation, everyone recognizes that as, like the quote unquote, correct pronunciation, and they recognize as the good English. But, you know, throughout the uk there are many dialects. And even though everyone recognizes received pronunciation as the dialect, if you speak received pronunciation in certain parts of England, you might come off as kind of crazy because everyone there speaks in a different dialect. But if you take that dialect and put it across the nation, a lot of people are going to be very opinionated on whether or not that is the correct way of speaking, because that's very regional. So there are certain modes of communication that are hegemonic. And suits, sport coats, a certain kind of, like, dressy kind of look is what I would consider hegemonic in visual aesthetics, even though wearing a short coat or wearing a punk rock biker jacket or other aesthetics can be legitimate in their own way. It's just that if you present that to other people, it's more controversial and fewer people are going to recognize it as quote Unquote, good, because it's so regional. The problem with, I will admit, when you talk about, like, the Midwestern guy, I get this a lot, is that somebody from outside of San Francisco or New York City or Los Angeles to say, I really like what you put out there, how can I dress like this? And that is sometimes a question I can't answer. Because if you want to wear sport coats and you live outside of a handful of cities, and especially if you fall outside of, you know, straight sizing, let's say you're a size 46 chest. I just got an email the other day. Someone has a 48 chest but a 32 waist. They're a professional baseball player. If you're that build and you are outside of the major cities, I don't really have an answer for you because tailoring has died over the last few decades. There aren't many good tailors. So what you're going to find is a lot of ready to wear tailoring, which is not going to fit an unusual build. And then you also have to be the kind of guy that's willing to wear a sport coat even though other people aren't wearing a sport coat. You have to put up with the fact that you are overdressed and you're doing it for yourself and it's pleasing to you. So sometimes if you're in a smaller city, there may not be a lot of options and there may be, I think, harsher judgments. Whereas I think in a big city, you have a certain kind of anonymity where you can dress very different from others and nobody cares. Like, nobody cares if you arrive to the office in a sport coat and everyone's dressed down. I still think you can in a small city. I have a friend who works for a religious organization. He lives just outside of Nashville.
- [15:09]
Sean
Yeah, Men musing, gentlemen musing.
- [15:12]
Derek
Yeah, menswear musings. Matt Mitchell. Yeah, he works for a religious organization and he wears a sport coat with jeans to the office. He told me that nobody in his office wears tailored clothing except for the really old guys. But he does it so often now that that's just like him. And one, he's obviously not going to get fired for it, but two, it's not like anyone comments on it anymore. It's just him. And I think it does take that kind of personality and it takes a willingness to really hunt for those ready to wear pieces to figure out how things fit. Because historically, men dressed well in tailored clothing, not because they knew all of this stuff. It's because they went to a local clothier, and that clothier, like, outfitted them. They, you know, you. You'd go to your clothier and you'd say, I have to go to a summer wedding. Or, I worked in this office, like, just figure out how am I supposed to dress? And that clothier told you, you're going to summer wedding. This is the thing that you're supposed to wear. And they'd figure out how it's supposed to fit, and they do all the tailoring and all that, and you walk out and you look amazing. Those clothiers have disappeared, and customer loyalty is no longer there as well. So whereas a man used to go to his tailor and would introduce his son to his tailor, now men shop from different places, not only different aesthetics, but they might buy their jeans from a jean company, shirts from a shirt company, socks from a sock company. Sometimes they're also buying the stuff online, where there's no sales associate to guide them. And then they have to figure out how to put together not only a good outfit, but also a good wardrobe and how to use that wardrobe to move throughout different social spaces.
- [16:52]
Sean
All right, my friends, I have a new podcast for you guys to check out. It's called Content is Profit, and it's hosted by Luis and Fonzie Cameo, and it's brought to you by the HubSpot Podcast Network. After years of building content teams and frameworks for companies like Red Bull and Orange Theory Fitness, Louise and Fonzie are on a mission to bridge the gap between content and revenue. In each episode, you're going to hear from top entrepreneurs and creators, and you're going to hear them share their secrets and strategies to turn their content into profit. You can check out a recent episode called the Secret to Content that converts and they break down our buddy Alex Hermozy's blueprint for effective video production. So you can check out Content is Profit wherever you get your podcasts. All right, you're telling me this, and I'm like, all right, I'm bought into all that, but I feel hopeless. So I live right outside New York City, so it's okay for me. I can go to New York City, but I still feel hopeless. Where I'm like, this sounds super intimidating. Finding a tailor.
- [17:51]
Derek
Yeah, there are solutions depending. Everyone has to figure out their own specific situation. If you're the guy that emailed me recently, he's a baseball player, 48 chest, 32 waist. You are absolutely not going to find anything in Ready to Wear or Made to Measure. You have to go to Bespoke, Most people are not that build. Most people are not professional baseball players. Most people are actually pretty average size. So they can usually get a good enough fit and ready to wear. I have some articles on, you know, where I think you can shop for a suit. But the issue is still that the effort is put on you. You have to figure out what are your fit issues, how do you want to dress, how to put together a wardrobe. Someone recently emailed me with photos of a poet. This person's writing an article about this poet's life. And this poet lived somewhere on the East Coast. Early in this poet's life, there was photos of him as a young person, I would say like in his 20s or so in the 1930s. And then over time, you see him in the 20s and 30s, he dressed really, really well, exceptionally well. I mean, average for the time, but looking back, like very, very well. And then over time, his dress started to worsen. And as I was explaining to this writer, if you can imagine this poet has an interest level in clothing, we'll say 70 out of 100 in the 1920s and 30s. He just has to walk down the block to get whatever he needs. And then over time, as tailoring disappears, it's harder to find good clothiers. And the number of options balloons. And there's all these different languages. A level 70 is only going to get you so far. Your interest level has to be 90 or 95 to get to how he dressed in the 20s and 30s. Because now you have to source things online, you have to do all this crazy work. There's a lot of burden now on the consumer, which is partly why it's difficult to build a wardrobe. It doesn't mean that another. A podcaster interviewed me once and they asked, do you feel that most people are badly dressed? And that's a very loaded question because I think there are many well dressed people, if you understand their own dress aesthetic and language. When I walk around San Francisco, I see people wearing cool hiking gear or vintage gear, but they're often like embedded in some kind of cultural community. But if you're outside of a cultural community that doesn't have much cultural capital, because that's, in my view, how we think of aesthetics. We think of, in terms of cultural capital and social language. If you're outside of those communities and you're not a punk and you're not a cool hiker or you're not part of a rock band or whatever, then you kind of have to figure out where to buy the clothes that Express an identity that you like and how it should fit and all of that. And, yeah, it's unfortunately a much harder uphill battle than it was 50 years ago. There's a really good. He used to teach business at University of California, Berkeley. I don't know if he still does. His name is Barry Schwartz, and he wrote a book called the Paradox of Choice. That book opens with a story of how Schwartz enters the Gap and is shopping for a pair of jeans. And the sales associate asks him, do you want washed raw, rinsed white, dark blue, slim fit, slim, straight, tapered, you know, baggy, athletic cut? And he gave him all these options. And he said he walked out that day from the Gap with the best pair of jeans he's ever bought. But he was left more unsatisfied than he's ever felt, because just knowing that there are so many choices made him question the choice that he made that day. And part of his book is that people are often better off if they're given a much more constrained number of choices. So if you think of, like, going into an Apple Store, there are very few choices, and they've constrained it to make the purchasing decision process easier. But they are. I mean, presumably they think so. They're all good choices. And the problem at the moment at the market is that there are billions of choices for any style of item following any number of design languages, any number of fits. And that has caused incredible anxiety in the market, which is very difficult to solve.
- [21:58]
Sean
Here's how I'm solving it is I go to your blog or people who I like or follow on Instagram, and I'm just like, I'm just going to do what they do. And, and. And it's sort of like when you learn how to play music, you play other people, you. You play other people's music for a long time, and then you start seeing, like, man, I love, like, this little riff from this rock, like, genre. And then I, like, I'm inspired a little bit by this thing, and I start crafting my own because I've just learned the technique and I know, like, what's cool and what's not and what's my texture with dress. It's kind of the same thing where it's like, all right, I'm new, so whatever Derek or whoever I follow on Instagram does, I'm just going to copy that. And in doing that, after a couple years, I'm going to develop my own sense. And so, like, the question I have for you, which is it's hard to Know when you're shopping online, which is what I think most people in their 20s and 30s do, it's hard to know what's good. And the reason why you need to know what's good is because if I were to follow what you and a lot of people say, I would be buying so much stuff. But that's not exactly what you're wanting me to do. I think what you and what I believe is that you should buy for life. You buy less things, but you buy high quality things that can last a lifetime. I still struggle to figure out what those high quality things are. And so my question is, how should I figure out what is a high quality brand or high quality product that is deserving of more money to be spent online?
- [23:23]
Derek
Yeah, all I agree with everything you said of find people that you like and copy them on the issue of how to find the quality things. So there, there are. It sounds like you've read a lot of my work, so I've written about different ideas of how we think of quality. There's the build quality. So there is such a thing as a certain kind of build quality with clothes. So to give an example, leather dress shoes. If you buy leather dress shoes made with a Blake stitch or Goodyear welt on the sole and the uppers are made from full grain leather, those shoes will age better, last longer and they can be resold.
- [23:58]
Sean
Like an Alden.
- [23:59]
Derek
Yeah, like an Alden. Versus if you buy something with a glued on sole and made from corrected green leather, that corrected green leather is a bad leather that's been sanded down to remove the blemishes or scars and whatnot and then coated with some chemical to make it look smooth and normal again uniform. And that coating eventually flakes off, doesn't age very well. So you end up looking at your shoes and you don't like how they look and then you go out and buy a new pair. Whereas full green leather will age better over time. It will look more natural. It gets the kind of patina that people like. And then with a stitched on sole, you can always unstitch the sole and replace it. You can actually still replace glued on soles, but it's a little bit more risky. There's only so many times you can do it. And I wrote an article on put this on how to judge quality and clothing and it runs through almost all of the categories. I mean, you know, except, except for like Gore Tex parkas. I mean generally speaking, sweaters, shoes, tailored jackets, you know, like woven shirts, things like that like how to think of quality. But the scope of build quality is actually pretty narrow. There are some things that are generally agreed upon as what is good build quality. To give an example, with tailored jackets, there are certain kind of ideas of what is a better or worse tailored jacket in terms of build quality. But some things are pretty subjective. And if a designer is trying to bring a suit or sport coat to market, they're working with a factory. And that factory has, let's say, like 300 operations. There is a certain gold standard for quality, quote, unquote. But a designer is often not trying to sell like a 5, 6, $7,000 suit. They're trying to sell a $2,000 suit. So they have to make design decisions on where to cut back, quote, unquote. And how they decide which part of those 300 operations to cut back is more is, I think, very subjective. But the real measure of quality should be, are you excited to put it on today? And do you think you'll be excited to put this on 10 years from now? That doesn't always mean wearing a classic aesthetic. It could be mean wearing something crazy because you like wearing crazy clothes. And then will this thing last to, you know, some degree? There is. There is like a certain kind of build quality in terms of will this thing last? If you buy something and it falls apart in two years, I think most people would want something that lasts a little bit longer than that, like as a physical item. So I think those things. Do you get excited wearing it? Will it last design wise and also kind of construction wise. And then also does it fit and flatter you when you put it on and you look at yourself in the mirror? Do you like how you look? And I think those basic points, Are you excited by the thing that you're wearing and does it fit and flatter you? I think gets you much further than thinking of this purely as an engineering problem. You can't just read specs off a sheet like when you're buying electronics. To some degree, it's more like food. When you bite into it, does it taste good? Are you excited to go out to that restaurant? I think that's a much more. A better way to approach things. It's a more holistic way to approach things than thinking of it just in terms of, is this well made?
- [27:16]
Sean
When I was kind of up and coming in my career, I didn't have a lot of money and, you know, I started my own business and, like, didn't pay myself very much. And so I was like, afraid to spend and buy things. Even though I, like, wanted stuff, you know, I was. But even after I made a little bit of money, I was still always nervous to spend. And so I see guys like you, you know, these writers who I, who I admire, and they've got like some great clothing. And in my head I'm wondering how many items do they actually own in their closet and how many? Like. Because, like, up until recently, I could have gone six months without buying a clothing item. Now I'm like, you know, I think on your blog you say, when you first get into this shit, even if you have money, buy slow, ease into it a little bit. And I'm like pulling myself back because I'm like, oh, I want to get this and I can afford it. And so I'm like, I want all this shit. How many things do you buy per month? And what's like a reasonable amount of spend, do you think, for someone who can, can, can afford these things?
- [28:16]
Derek
Well, I do spend a lot more than the average person. I admit that. I don't know the exact number. But to give an example, I recently bought a hoodie from bare knuckles. I bought two RL flannel shirts.
- [28:29]
Sean
RRL flannel shirt is what, two to 400?
- [28:33]
Derek
No, no, I wouldn't, I would never have bought a $400 flannel shirt. I think I spent, I want to say like 175. I bought a pair of Bryceland cargo pants. Those were kind of expensive. Those were like 350. But I've been lusting over them for like a year, so I finally just bought them. That's for this season. I don't really imagine myself buying much for the rest of the season. So, you know, I think most people are not buying two shirts, a hoodie and a pair of pants twice a year because I break up my shopping into seasons, Spring, summer, fall, winter. And then I do use a lot of custom tailors and I usually have like a suit or sport coat in the works through a custom tailor. And that's been true for a while. So you know, again that most people are not doing that.
- [29:21]
Sean
Those suits are getting tailored. Are those bespoke or are those off the rack that you're getting fitted to?
- [29:26]
Derek
They are bespoke.
- [29:27]
Sean
That's interesting. That has always intimidated me because it seems like it's a pain in the ass of a process. And according to. You have one post on your blog, you're not sure if you can even tell the difference all the time.
- [29:38]
Derek
Yes, I had this friendly argument with a Good friend of mine who strongly feels that you can tell, I will say I was in a dm. I am in a DM with some guys who are into clothing. And we were looking at a politician's suit and we all suspect that he's wearing bespoke because of the stitching and the styling and all that. And we can, and we can kind of pinpoint the region of where the.
- [30:02]
Sean
Tailor'S from, but potentially this person is wearing like $5,000 suits is what you're saying.
- [30:08]
Derek
I would estimate that their suit probably cost around 3 to 4,000. And then I checked their Twitter account and they follow me. So I was like, maybe they do buy piss book suits, so maybe you can tell. But, um, I, I'm still very skeptical of whether or not, generally speaking, you can tell the difference between readyware and bespoke. And I completely agree. I think bespoke is a huge hassle. Um, there's more Mrs. Than people let on online. I think it's very important when you go into that space to know that, like, not all commissions turn out well. It's often pretty common that commerce commissions turn out poorly, even if you're using a good tailor. But there are a lot of bad tailors. One, there are some people who need bespoke.
- [30:48]
Sean
We have to define it is the terminology like off the rack. And then one up from that is like made to measure, which is I guess a suit supply. And then is bespoke purely from scratch.
- [30:57]
Derek
Well, the short answer then is ready to wear is what you go into store and can touch and feel and put on yourself and put back on the rack. Made to measure is something that has a block pattern, which is a pre made pattern that they adjust given your measurements, you're measured, and then they adjust the pattern, make the garment straight to finish. And then you come in for what they call one fitting, which means they put the garment on you and they figure out, you know, what needs to be changed. That fitting is basically not that much different than putting on a ready to wear garment. And they do adjustments. The only sometimes difference is that in a made to measure garment, they have more inlay, which means there's more room for adjustment. And then bespoke, theoretically is that the pattern is produced from scratch. And then there's a series of fittings, typically three basted forward and final fitting. And then it's sort of like you can imagine it as someone sketching, like when you're, you know. When I was in art class in high school, they taught us, like, do a Sketch and then you kind of like fill it in and then you kind of work it out. Fitting is sort of like that. The tailor sketches out what they think is going to look good and then does a fitting and figure out what adjustments needs to be made. And then through that iterative process, supposedly you wind up with a better garment. Reality is a little bit more complex than that, but that is, that's the general contours.
- [32:15]
Sean
But your recommendation is for most people, is it ready to wear and that you get tailored?
- [32:22]
Derek
Absolutely. Ready to wear. Because few reasons. One is that most people are straight sized, meaning they can fit into a ready to wear garment because those garments are made for the average sized person. And then two, the tiny differences. You're probably not as obsessed as I am with like, oh, like the quarters are not open enough and like the shoulder is. You know, you probably, you probably are not like obsessed over those things. Even if you are obsessed with those things, you have to like realize that like 99% of people seeing you are not going to see those things. And even if they do see those things, you have to be standing like a robot for someone to spot those things. In real life, you move around and you're sitting and you're interacting with the world. So like all of the things that people are talking about, including me, those disappear. And then the third thing is that most people don't care about the craft element. And even if they do think they care about the craft element, they probably can't even spot it. So like, can you tell the difference between a machine made buttonhole and a handmade buttonhole?
- [33:19]
Sean
No, of course not. Very few people can, I think.
- [33:22]
Derek
Yeah. So like there are some people who need bespoke, and those are people like John Fetterman will never be able to fit into an off the rack garment or even made to measure because he's very far from the average sized person. He would have to go bespoke if he wanted a suit that fit. But most people are not that person. And the most important reason, the top tier reason of why everyone should try ready wear first, is because you can try on the garment and put it back on the rack. Nothing happens at the end of the day. Whereas with a custom garment, if the tailor offers you a money back guarantee, they're not a good tailor, no good tailor will ever offer that because it takes a lot of time, effort and money to produce a good suit. And then if there, if it's final sale, that means that if you put it on, it might not fit well. There's no guarantee that's going to fit well. But even if it does fit well, you might not like the silhouette. You might have chosen a crappy fabric, maybe you asked for dumb details and then all of a sudden the garments produced and you look at and you realize, oh, this actually looks horrible. There are many things that can go wrong. And then at that point you've just spent anywhere from, you know, like two to $8,000 possibly for a garment and you can't return it. Whereas with the ready wear garment, you can try on a 10,000. I don't even know if $20,000 suits exist for ready to wear, but if they did, you could try it on and put it back on the rack and nothing happens. And that's the number one reason. Even if you are just getting into this and you suspect that you need a custom garment, I still think you should try ready to wear it. Because when you try ready to wear, you can start to identify certain things. You can start to say, oh, I actually don't like how I look in a very soft shoulder jacket, I think I need more padding. Or I don't actually like how I look in a three button jacket, I think I want a two button jacket. And once you start getting an eye for that silhouette, you can then start to find a tailor. Because if you know that you want a very padded cut, that narrows your options.
- [35:26]
Sean
So here's the deal. I made most of my money from a newsletter business. It was called the Hustle and it was a daily newsletter at scale to millions of subscribers. And it was the greatest business on earth. The problem with it was that I had close to 40 employees and only three of them were actually doing any writing. The other employees were growing the newsletter, building out the tech for the platform and selling ads. And honestly, it was a huge pain in the butt. Today's episode is brought to you by Beehive. They are a platform that is built exactly for this. If you want to grow your newsletter, if you want to monetize a newsletter, they do all of the stuff that I had to hire dozens of employees to do. So check it out. Beehive.com that's B E E H I V dot com. I have a tailor now and I don't know if I like, like, it's kind of funny. First of all, a lot of tailors. Is it a red flag if your tailor dresses poorly or has poorly fitting clothes? Or is it like one of those things where it's like the cobblers kids is the last kids to get shoes. You know what I mean?
- [36:29]
Derek
Yeah. It's a cobbler's kids. Last kids. There are many tailors who. Who also dress poorly because many tailors are better thought of as technicians. They're not like stylists. So they themselves are often just wearing something that's not very interesting. So I wouldn't judge a tailor's work by how they dress, but I would judge a tailor's work by the customers that come out. So if the customers come out and they all are wearing suits that don't fit, the chance of you getting a good suit from that tailor is very low. But if all the customers walk out and their suits fit perfectly and especially helps if the customers walk out or have a similar build as you. So if you are a very heavy guy and you see heavy guys walking out store and they all have suits that fit beautifully, well, then, yeah, the chance of you getting a good suit from that tailor is very high. Obviously you're not going to stake out a tailor shop and like, just, you know, like walk, see who comes out the door. But you can do this on Instagram. You can go to Instagram, go to the tag section and, you know, see if the people that wear their clothes, if their clothes fit well.
- [37:32]
Sean
Yeah, I, I like to collect old denim. So I was. I've been into salvage and raw denim since probably 2008. It's kind of a weird hobby.
- [37:44]
Derek
Oh, so you are not new to this. If you, if you were into Denmark in 2008, you are actually. You're very seasoned and so you know this stuff very well.
- [37:51]
Sean
I. Denim is my pet. I'm, I'm. I'm an American history nerd. I'm very passionate. So have you ever seen a TV show, American Pickers? Yeah, I used to work with Mike when I was in college. That was my college job, was working with Mike from American Pickers. And so I got. And I'm obsessed with American history. And there are two, two or three things that are very American are denim and the leather jacket. And so I've always owned shot leather jackets or I've always wanted that. Or Buco leather jackets.
- [38:23]
Derek
Yeah.
- [38:24]
Sean
And then like red tag Levi's or Big E Levi's. I was one of the first customers of Imogen Willie, and I would spend, like, ungodly amounts on denim. And I would say, I have them all saved. I have dozens of them saved because I want to. I read Heddles and I've like, been the fate of the Fade Friday.
- [38:42]
Derek
Like, anyway, you were, you were presenting Yourself as new to this hobby, you are as seasoned as to come. Anyone who says all of those words, Heddles and Imogene Willie and you know.
- [38:54]
Sean
Shot well Mad Carey from Imogene. Like, I used to go to the store all the time. I didn't have any money and they would kind of pity me and give me a shirt every once in a while. And then like when I started making like $10 an hour somewhere, I would like, I bought my first Imogene and I would get shrink to fit Levi's back when I was 18. I love that shit. But as I got bigger, I'm into weightlifting and so my legs got too big for a lot of these like traditional stuff. So I've then I used to go to Self Edge in SF and get flathead. That was anyway the Japanese shit I love. And so my point being, I spent all this money on denim and what I've. And it's sort of like you start as a beginner where you buy cheap shit and then you go in the middle, which you buy really expensive high end stuff. And then now I've sort of ended on the other side to where I'm just buying $30 Wranglers that fit well and so. But like with, with. With tailoring stuff, that's what you've inspired me with is tailoring stuff. I'm kind of new to where I'm buying the cheap shit thrifted stuff that, that I could tailor. That's actually pretty dope. But then I'm like going to like suit supply, which is like the thousand dollar shit. And I'm like, it kind of fucking sucks. Like I should either like go to like keep the cheap dude, cheap thrifted stuff that you get tailor or go.
- [40:08]
Derek
Like pretty high end that journey what you're talking about. Imagine if you started that denim journey and you're buying like 21 ounce iron hearts.
- [40:18]
Sean
Yeah.
- [40:19]
Derek
You would probably not even get into it because you'd be like, no, it's insane.
- [40:22]
Sean
Who would pay the buy.
- [40:24]
Derek
Yeah.
- [40:24]
Sean
Yeah.
- [40:25]
Derek
The only way that you end up buying 21 ounce Iron Heart Denim is if you start with 14 and you like how they feel and then someone says, oh, why don't you try 16 ounce? And then you, you like, you really like how that feel. Then you move up and all of a sudden you're at 21 ounce and then you like. I actually do like this, even though it's. No sane person would ever like this. But it's just because I'm in this hobby. So that's to me, the same with rated wear with tailoring is that you start, you have to figure out what you like. There's a really good book that I like. It's called Perfumes the Guide by Luca Turin and Tanya Sanchez.
- [40:59]
Sean
A book on perfumes.
- [41:01]
Derek
Yeah, but it's just, it's just a list of reviews. So it's only helpful if you. If you're into perfumes and you want to look up a review of what someone thinks of a perfume. But in the introductory chapters, Tanya Sanchez writes, I've talked to hundreds of people who are into perfumes, and they all seem to follow a similar journey. In the beginning, there's this exploration stage where you're like, finding perfumes in, like, your mother's wardrobe or your father's dresser or whatever. And then you explore different notes. And then there's the stage where you think you've found your taste and you have very rigid rules about everything. You have very strong opinions. And then the third final step is what she feels is nirvana, where you know the rules, but you're not, like, strict about them and you just like what you like. So I think that's actually pretty true for a lot of things, whether you're into motorcycles or whether you're into, you know, you're a foodie or you're into fountain pens, is that people start with an exploration stage. They figure out the terrain, you know, the hills are over there and the lakes are over there. And then they get very adamant about rules. Like, everything has to be this way. And then there's a point where they just know what they like and they're not as adamant about the rules. And sometimes the things that they like are not even the expensive, coveted things that everyone talks about. It's just something they like. And that's it. That's the, that's the emotional. That's the nirvana that you reach. So the thing that you like might just be wranglers.
- [42:29]
Sean
It's just a pain in the ass that you have to spend as much money, that much money, and a decade to go through this. And that's why, I mean, that's why I like reading your blog. And reading people like you is like, I'm like, how can I just like speedrun some of these learnings and just not make the mistakes that I've made before. Like, for example, a big thing in clothing that, that a lot of people are bringing back is high rise trousers. And like, there was this period where we went through, like, slim clothing. And first of all, it's the fucking worst. Because it looks stupid looking back on it. And it's like, incredibly uncomfortable. And like, half the dude, half of men can't, like, they have big asses and big thighs. Like, we can't wear that stuff. Like, you can only wear that stuff if you're a smaller person. But it's like, I just wish I would have, like, stuck to more timeless things and thought what will. What was cool 50 years ago and will likely be cool in 50 years from now or what I think will be cool. And I just wish I wouldn't have gone through that. That, that slim phase. Because now I have so much slim stuff and I've spent tens of thousands of dollars probably on it.
- [43:38]
Derek
Yeah, I mean, I will say that that high rise fuller leg look I often talk about online in the context of tailored clothing. If you're. If you want to dress like Mick Jagger and rock and roll, kind of like, you know, tight leather jackets and tight rock T shirts, then you need tight pants.
- [43:53]
Sean
That only works if you're a small. If you're a smaller person, by the way, I don't think I can.
- [43:58]
Derek
You have to be a very slim dude.
- [43:59]
Sean
If you're above 510 and over, like 180, it's hard to pull that off because you just look like you look stupid. And I've tried to do that and I look so dumb.
- [44:09]
Derek
I do think it helps to be a certain build for that look and then the whole look has to come together. You have to, again, think of it in terms of like a social language thing. But if you're wearing a tailored jacket, like a suit jacket or sport coat, I do think there are certain proportions for the trousers that work better for the jacket and especially works better across a wider range of men. There are some men who can wear very, very skin tight suits, but they are often very thin and they usually have very broad shoulders compared to the waist. They're basically models. Like, if you look at Runway models that are wearing those suits, they do look good, but most people are not built like that. And a jacket can only be as tight as your body allows. So at some point you have to figure out how to create a trouser silhouette that works with the jacket that you're wearing. And the jacket is constrained by your own body's proportions.
- [45:00]
Sean
I appreciate you coming on this podcast. You're the man. And thank you for everything.
- [45:04]
Derek
Thank you. Thanks for having me on. This was such a, such a pleasure to be on. So thank you for the opportunity.
- [45:09]
Sean
Thank you. And that's the pod I feel like.
- [45:11]
Derek
I could rule the world I know I could be what I want to I put my all in it like no days off on the road let's travel never looking back.
- [45:24]
Luis
Hey, Sean here. I want to tell you this little story about Winston Churchill. So Churchill once said, first we shape our buildings, and thereafter they shape us. And I think this is true not just for the buildings we see in cities, but also for the building blocks you choose in your company. For any company that I start, I use Mercury for all of my banking needs. Why? Well, it was built by a YC founder and you could tell this is built by a founder who understands the needs of other founders. Second thing is, it's modern, it's clean, easy to use. The design is really nice. You never have to drive somewhere, park, put coins in the meter, get out. Just to do one simple task. You can do everything in just a couple of clicks. They got bill pay, checking account, savings account, wire transfers. Everything you need, they got it. I use it for not one, but actually six of my companies right now and actually even have a personal account with them. It's kind of amazing. So if you're ready to operate in the future, head over to mercury.com. apply in minutes. Disclaimer Mercury is a financial technology company out of bank banking services provided by Choice Financial Group and Evolve bank and Trust members. Fdic. Thank you to Winston Churchill for that little ad segment. All right, back to this episode.