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Please enjoy one of our favorite episodes from the Dressed archive of over 500 plus shows.
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The history of Fashion is a production of dress media. With over 8 billion people in the world, we all have one thing in common. Every day, we all get dressed.
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Welcome to Dressed the History of Fashion, a podcast that explores the who, what, when of why we wear. We are friends, fashion historians and your
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hosts, Cassie Zachary and April Callahan. Duress listeners. Don't call it a comeback because we have been here for years. We are coming back at you with part two of our episode on Hip Hop, Style and Caswell. That was a very admittedly cheesy way to start our episode today. I did so because I have a very fun LL Cool J Story if you want to hear it. I was obviously quoting him from Mama said knock you out.
E
Yes, please tell.
D
Okay, well, many years ago back in the 2000s, I put myself through grad school waiting tables working as a server at one of New York City's super trendy hotspots and we had a ton of celebrity clientele in there. All the time.
E
And.
D
And for some reason, unbeknownst to me, LL Cool J took a liking to me because he would come in all the time, and then he started requesting for me to be his server when he and his friends would come in. And he would come in with his family and his kids, and they were always so warm and so lovely and really just a pleasure to take care of. And so one night they came in and he was with his wife and his kids, and he was like, hey, April, when she gets here, I want to introduce you to my friend Mary, who's going to. To be joining us tonight. And I was like, okay, cool. You know, but, like, I was also, like, running around doing stuff like getting them drinks and, you know, getting them ready for the night. And then when I came back, their guest was there. Do you want to guess who it was?
E
K. I'm going to go out on a limb here and say Mary J. Blige.
D
It sure was.
E
Wow.
D
So I'm. And I'm just like, double swoon, right?
E
How exciting.
D
Yeah, yeah, yeah. It was. It was really fun working there. And it was actually like that quite a lot. Everybody who was anybody kind of rolled through there at one point or another, you know, from JLo and Diddy to Ice T, Nelly, 50 Cent, Kelis. I took care of Alicia Keys on the night that she won her Grammy Award for Empire State of Mind, which was very, very cool. And it was always really fun to interact with all these amazing R B and hip hop artists. And of course, you know me, I was always super excited to see what everyone was wearing. Their singular style being part and parcel to their identity as artists.
E
Yeah. And those very intersections of style, fashion, and the hip hop identity. That is, of course, what we are here to discuss today as we continue our talk with Elena Romero and Elizabeth Way, co curators of the exhibition fresh fabulous 50 years of hip Hop Style, which is currently on view now at the Museum at FIT in New York City. The through April 23, 2023. And Liz is an associate curator at the Museum of FIT at the Fashion Institute of Technology, where Professor Elena Romero also works. Elena is an assistant professor and the assistant chair of the advertising, Marketing, and Communications department, and for the past 25 years, has also worked as a TV, radio and print journalist specializing in covering fashion and culture. So without further ado, we pick up our discussion with one of the most iconic of Hip Hop garments, Sneakers.
D
We have to talk about sneakers and we have to talk about footwear. I know in the exhibition that not all of the footwear featured is our sneakers. So maybe we could just mention that very briefly. But let's do talk about kicks for any of our listeners out there that are. That are sneaker heads.
C
So I will say I am certainly not an expert on sneakers. I know there are people who know it so, so, so well.
D
Right.
C
And so, and there have been really amazing exhibitions that focus on sneakers, for example, at Brooklyn Museum. So we definitely had to include sneakers because it' one of the ways that hip hop, it's one of those genres that hip hop really amplified into a huge kind of aspect of fashion that it wasn't before. So we do include iconic pieces. For example, the Adidas shelled hose, the Nikes with Michael Jordan. And then we also use sneakers to talk a little bit about kind of different aspects of hip hop. For example, we have a pair of the four Baltimore Air Force One designs. And Elena talks about this in the book, that Air Force Ones were debuted by Nike, and they didn't. They didn't last very long. They were only gonna keep them in production for a couple of years. But people in Baltimore, specifically three sporting goods stores in Baltimore, had such good sales that they approached the president, Phil Knight of Nike, and asked if they could take over production and continue to sell them exclusively. So Phil Knight sold them the production, and for a while, you could only get Air Force Ones in Baltimore.
D
I had no idea. All these little hidden histories and these
C
sporting goods stores, you know, they would release different colors, the swoosh in different colors, the matching strap on the ankle. And people would match their ensembles, match their tracksuits to their Air Force ones. And people would come down from New York or up from D.C. to get them. And then after that, Nike kind of re expanded production internationally. But we wouldn't have Air Force Ones. It wasn't for these three retailers in Baltimore. So Nike released in 2017 a 4 Baltimore edition to pay homage to that story.
D
Wow.
C
We also have a pair of Reebok 5411s. So these are the Reebok Freestyle. That was a dance sneaker designed for women. It was one of the first sneakers designed specifically for women. And it came in all these bright colors, but it's called the 5411 because that was its cost plus New York sales tax when it was debuted in the 80s.
F
I would get mine at Vim, by the way. And that was also one of the very common retailers in our neighborhoods. Yeah. So $54.11 was the final cost. And it became the slang term that if you were from an urban city. And you said 5411s. You knew exactly what shoe you were talking about.
D
Yeah. So that wasn't Reebok's initial name of style, the freestyle.
C
But both of these stories tell this story about how hip hop is local. It's about your neighborhood, it's about your city. And all these different cities have different styles. We really focus on New York City because we're here. But there's so many other stories that we could tell. Not just about Baltimore, but, you know, Atlanta, about la, about Detroit. There's so many different hip hop stories, and it's so specific.
D
Well, you know, this nexus of high fashion and hip hop is a total given today. But this wasn't always the case. So when and where do we start to see hip hop artists themselves jumping into the game in terms of fashion brands?
F
That happens more closer to the late 90s and early 2000s. So I'm kind of gonna backtrack a little bit. Oh, yeah, please do. So what we end up seeing is there's a direct connection between the hip hop music becoming mainstream.
E
Right.
F
The popularity of the hip hop Persona, and then hip hop artists recognizing the branding and the power that they have in, you know, the image that they're creating. Early artists like Chuck D and Naughty by nature and Wu Tang Clan realized that they were only making but so much money off of concert merchandise and catalog sales, right? So what they ended up doing is kind of taking control of their image and moving from concert merchandise to creating catalogs and then eventually venturing out and creating their own brands. So we start seeing that really, really early on, in the early 90s. Then we start seeing music mogul. So it was artists. It was music mogul. So early on, you're seeing Russell Simmons with Fat Farm, and then later down the road, you see Sean Puffy Combs, Love Combs now with Sean John, and then Jay Z and Damon Dash with Rocawear. Those brands were very significant because at the time that they were launched, they were at the height of the music game. So we saw instant connection with fans.
D
Right.
F
But that was almost a direct correlation. The Rocawear was a direct correlation to the record label. Puffy decided to take a slightly different approach by not naming his clothing brand, let's say, Bad Boy Gear, for example, and focusing on Sean John now, placing the attention on his personal sense of style, his swagger, and how that may then impact the end consumer. And we see that now with celebrity artists like Rihanna.
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Right.
F
And her Fenty brand kind of Taking that mantra ahead.
D
Yeah, yeah. And he won like at least one CFDA award, if not more than one. Sean.
C
Sean Films was the first black designer period to win a CFDA designer of the year award. And the next designers of color to win were the guys from public school who met and trained at Sean John.
D
Yeah.
C
So it really is an important brand in breaking into the fashion industry. For so long the fashion industry kind of ignored hip hop brands. You know, they were young men's brands. They were by people of color. But Sean John and also Fubu who had these really massive celebrity packed fashion shows at, at Bryant park, when the shows are still at Bryant park, they really broke into the fashion industry.
F
Well, Cross Colors as well as Fubu had different spokespeople attached to their brand. You know, a very young Dijiman was part of Cross Colors spokesperson. And then you have an LL Cool J who signs on with fubu who was both in television and film and music. And that kind of now elevated the brand status of these young men's. Now to have celebrity spokespeople, we start seeing the influence of hip hop moving the celebrity from the front row also onto the Runway by designers like Tommy Hilfiger who would have Coolio and Tresh on the Runway and a number of of other folks as well.
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Fashion becoming so important at that moment. A lot of these stars are of course gonna need assistance. So I'm hoping that we can talk about the role of the stylist within hip hop. June Ambrose has actually already been on Dressed in the past. We talked a little bit about her work with Jay Z and Missy Elliott, but I'd like to know more about some of the other influential stylists that were working in the genre.
C
Well, we were really lucky to work with Misa Hilton. So she came in for an interview and she lent things from her personal archive. And, you know, she started working at Uptown records in the 90s when she was still a teenager. So she and Sean Combs worked together. And she was really influential in changing the look of, like, groups like Jodeci, which were R and B artists that were kind of drawing from a more, you know, even 1960s kind of conception of what an R and B group would look like. And she wanted to give them, like a harder edge, rock and roll, rap inspired feel, which, you know, not what Uptown Records had envisioned for their hip hop artists at that time. But she also worked with Mary J. Blige and later Lil Kim. And so she's so, so important in shaping what hip hop looks like. And, you know, I think of probably when she started, the word stylist was probably not used to describe her, but she was dressing these people. She drew from her own kind of sense of style, which was very strong. And she was hustling. She, you know, brands were not opening up their showrooms to her for music videos, for events. She was putting looks together from the looks that she Grew up with around the way looks that inspired her, but also kind of. She was also a designer. She was also making custom looks. And it's much, much later that she becomes a global creative partner with mcm. And we were really lucky to have the boostie that she made for Beyonce for the Apeshit video that she made in partnership with mcm. And so we see how she. Her creativity has just grown and grown and grown. And as hip hop artists have been recognized, her resources have also been able to grow.
D
Right. June talks about that when we chatted about that specific moment when all the floodgates opened and all the fashion brands were like, what do you want? The world is your oyster.
C
It took them a while to realize the power of hip hop and hip hop celebrity.
D
Yeah.
F
So many early stylists can be attributed to working with Sean Combs during his different record label from Uptown to Bad Boy stylists like Cybil Penix, Groovy Lou Jones, June Ambrose and her Mod Squad. Hence, we start seeing the role that 5001 Flavors plays in the customization. A lot of the custom leather stuff that you see comes from 5001 and Bad Boy collaborations. And then in more recent times, stylists like Monica Murrow, who's responsible for the pink fur that Cam' Ron has forever embedded in our heads that Drake recently wore performing at New York's Apollo Theater.
D
Mm. Pink is an incredibly popular and influential color. There's an entire little section of your book dedicated to it. Do you wanna touch on that very, very briefly?
F
Sure. So a couple years back, the museum had done a symposium and an exhibition around the col. And at that particular time, Dr. Monica Miller and I were able to do a talk. We didn't have the chance to write a chapter for the pink book, but it was something in the back of our minds. And so when this project came along, it just made perfect sense to explore it. And we had already done some of that research. And it was so much fun to work together to really talk about all the different hues of pink, which is really unisex. And we've seen it with hip hop musicians with the pink polos to, you know, baby pink fuchsia, and every color in between in that hue.
D
Yeah.
C
And one of the things that was really interesting about what you and Monica write about is that, first of all, men in communities of color were less kind of indoctrinated to the idea that pink was only for girls.
D
Yeah, Right. That it was gendered.
C
That was certainly an idea that was there, but it was much Less adhered to. And male style was something that was really important in these communities. So we see male rappers much more open to the idea of wearing pink. And then what's also interesting is that because of this idea that female rappers had to be tough, they had to be androgynous, they had to keep up with the guys. It's much, much later that we see female rappers embrace pink. And when they do, it also becomes kind of this rebellion. So when like, you know, Foxy Brown and Lil Kim are wearing pink, it's like an unapologetic embrace of their femininity, which was pretty new and rebellious for hip hop. So pink kind of works as this rebellious color for both genders, Right?
D
Right. Well, I think especially lately, there's been some really provocative play around gender on the red carpet on the stage by hip hop artists, probably most notably to our listeners, Lil Nas X. So blurring these kind of gender lines is nothing new. It's been there since the very beginning.
C
Absolutely.
D
But do you want to speak a little bit more about how just the gender paradigm in general has kind of been historically handled within the fashion?
C
Well, women in hip hop, I think early on were the ones pushing this more androgynous style, and it was out of necessity. I think it's more recently that we. And you know, it's Gen Z, like, they have a lot of different ideas about gender. You know, they're breaking away from old ideas. And so people like Lil Nas X or, you know, we have young thugs, Alessandro Tracon ensemble that he wore on the COVID of his Jeffrey album, that was a collection all about androgyny. So I think when we see kind of men embracing more androgynous styles, that is coming from the younger generation.
F
And you are wearing a cross color shirt with TLC on the COVID which is very interesting because they wore a lot of cross colors, which again, was a brand that was kind of unisex. And then they would add all these different elements to kind of play off that. Right. They, you know, you would see a condom on an eye. You know, again, just kind of almost poking fun of, you know, traditional masculine roles. Yes. In the early days of hip hop, women had no choice but to downplay their femininity because they wanted to be taken seriously as artists of their craft. Little by little, as they get more popular, we start seeing more comfortability in that expression. So what was once maybe the baby hairs and a hairstyle or, or using custom jewelry, having jewelry exposed, then we start seeing kind of this hybrid, like a Salt and pepper, where they're wearing that lycra spandex outfit underneath the Dapper Dam custom jacket. And then, of course, once we get the next wave of hip hop artists, that is a little Kim going full thrust with, you know, presenting her femininity and her power and her prowess, you know, full head on.
D
Yes, yes. And another expression of that is, of course, all of the incredible beauty trends that are coming out of hip hop. Elena, you write specifically about some of the iconic hairstyles in the book. Liz, you write about nail art. Do you want to mention these very briefly before we sign off today?
C
So nail art is definitely something that communities of color and hip hop specifically kind of brought into the wider. The wider culture. And, you know, nail art is everywhere now.
D
Yeah.
C
But we have people like Bernadette Thompson, who in the 90s, made little Kim's money nails. It was originally made out of real US Currency. And someone from the treasury contacted her and let her know that not maybe faux currency was a better choice for that. But, I mean, so she kind of came up with so many ideas that we see in nails today. And in the exhibition, we have two sets of nails made by Jenny Boy, who does Cardi B's nails. So, like the stiletto dimensional, crystal, sparkly, bejeweled nails, we have two amazing sets. And, you know, that's something that is such a style statement, and it gets so much attention on social media and in popular culture. And that's definitely something that women in hip hop kind of made popular.
F
Hair or that layer of is a very strong statement for both men and women alike. The chapter that I touch upon on hair tries to look at both genders. So many historic and iconic hairstyles that I can think of, from, you know, the slope gumby to the mushroom cut for girls and all the looks that we've seen on the Runway. Right. From dreads to baldies to platinum blonde.
D
Well, we are about out of time for today. I want to thank you so very much. I have one last question for you. The exhibition opens next week. I have not yet seen it. Personally, I'm very, very excited. You've mentioned several pieces that are in the show, but do either of you have a couple favorite pieces that or stories surrounding those pieces that you mentioned before we go?
C
Well, two of my favorite pieces are in our hip hop, glam or kind of red carpet section. We have the moschino gown that Megan Thee stallion wore to the Met Ball, I believe, in 2022. It's absolutely gorgeous. It's in gold with a little shrug, with leather, feathers, and sequins. It's an absolutely gorgeous piece that really shows how hip hop artists, especially women in hip hop, have become the kind of fashion icons. It's absolutely regal and gorgeous. And then another gown we have is the Thierry Mugler white fringed gown that Cardi B wore when she won her Grammy. And so this is a vintage gown from the 90s. She's been working with the Thierry Mugler archive, and so. So she's had so many iconic looks, like, connected to it, but it's just, again, another example of how important hip hop celebrity has become to pushing fashion forward. This partnership with Thierry Mugler is a huge part of kind of the 90s coming back and recontextualizing it. So it's really. I think it's a great way to end the exhibition because it really shows how far hip hop has come into influencing mainstream fashion.
D
Absolutely.
F
I have quite a number of favorites also. One of my favorites comes from our red carpet, and it's won by chance the rapper, and he's wearing Ralph Lauren. And it's a custom piece that speaks to the stadium collection, which was very, very important in the early 90s. And I love the idea of kind of mixing this idea of athletic sportswear with tailored clothing to be able to show the versatility of what hip hop style could look like. So many people, I think, are so accustomed to thinking of hip hop style and as the 80s and baggy and logos, and that's still gonna be always, to some degree, a component of that. But how has that evolved over time? And I think that particular piece speaks to that evolution.
D
Yeah. Somebody asked me yesterday what I was gonna wear to the opening, and I was still kind of, like, debating a little bit, but I think I finally settled on. I have this really beautiful vintage, kind of bright orange and navy blue tartan dress. It's very long, but I'm gonna layer it with a dapper Dan sweatshirt. Perfect.
C
I love evening wear, casual wear. I mean, this is such a hip hop look.
D
Ladies, thank you so much for your time, your incredible exhibition, and your incredible book. We can't wait for more.
C
Thank you so much for having us.
F
Thank you so much.
E
Alaina, Liz, thank you both so much for your book and exhibition and sharing them both with us this week on Dressed Listeners. We doubt this will be the last you hear about hip hop style and fashion this season. The actual 50th anniversary doesn't happen until August of 2023, so don't be surprised if we have a few other things up our sleeves. Stay tuned. So don't forget you can get your hands on Liz and Elena's book Fresh by Fabulous 50 Years of Hip Hop Style if you can't make it to see the exhibit before it closes on April 23, 2023. Otherwise, I think that does it for us this week Dressed Listeners, may you consider how hip hop as a influence the fashion in your closet? Next time you get dressed,
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We get so many questions from you all about our recommendations for fashion history books, so if you're interested you can always find a link in our show
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notes to our bookshop.org bookshelf so that adds address is bookshop.org shop forward/dressed and
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there you will find over 150 of our favorite fashion history titles.
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Thank you as always for tuning in and more Dressed coming your way soon. The History of Fashion is a production of Dressed Media.
Episode: Fresh Fly Fabulous: Fifty Years of Hip Hop Style, an interview with Elena Romero and Elizabeth Way, part II (Dressed Classic)
Date: July 3, 2026
This episode of Dressed: The History of Fashion delves into the intersections of hip hop culture and fashion, celebrating the 50th anniversary of hip hop style. Hosts April Calahan and Cassidy Zachary continue their conversation with Elena Romero and Elizabeth Way, co-curators of the exhibition Fresh, Fly, and Fabulous: Fifty Years of Hip Hop Style at the Museum at FIT. They examine the evolution of hip hop fashion, from neighborhood styles to red carpet glamour, discuss the influence of key designers and stylists, and highlight the genre’s enduring impact on broader fashion and cultural norms.
The episode beautifully illustrates hip hop’s journey from grassroots neighborhood style to the apex of global fashion. Through the insights of Romero and Way, listeners gain a multifaceted view of style as local identity, commercial power, creative rebellion, and, ultimately, high fashion. The role of community-driven innovation, the struggles and triumphs of Black creatives, and the ongoing expansion of gender and beauty norms all emerge as central to the hip hop style story.
For a deeper dive: