Fashion History Forgot the Black Women Who Invented Streetwear

From logomania to Timberlands, the women who originated these styles on NYC streets deserve to go down in fashion history. Here, they set the record straight.
By Hillary Crosley Coker
Feb 01, 2021 @ 8:00 am
Each product we feature has been independently selected and reviewed by our editorial team. If you make a purchase using the links included, we may earn commission.

As the world remains inside to stay as safe and healthy as possible, fashion trends have largely moved from aspirational to functional and most importantly, comfortable. This is where contemporary streetwear shines. From Melody Ehsani's comfy sweatsuits to Bephie's Afrocentric graphic tees, each company's causal silhouette says, I might not be "dressed up" for this Zoom meeting, but I am killing it, on my couch. And while fashion's rising tide of ease might be new, streetwear's origins in Black culture are not. 

In fact, in the late 1980s and early '90s when this fashion genre was born on the streets of Black and Brown neighborhoods, it was called simply "urban" wear donned by fly girls. But now, since their styles have been emulated everywhere from high fashion runways and glossy magazines like this one, it's time to revisit style history and make sure credit has been given where due. "We have to be really intentional and proactive about telling the truth so that history isn't written another way," says April Walker, innovator of the all-denim look, whose line Walker Wear was worn by Method Man, Notorious B.I.G., Tupac and more. 

Ahead, she joins five other Black women who were instrumental in the early days of East Coast urban wear, putting together outfits you've probably always treated as pop culture canon without really knowing why. You know their styles — you probably still wear some of them today. Now, it's time to know their names.  

Credit: Design by Jenna Brillhart. Images by Getty Images, Courtesy.

Misa Hylton

Misa Hylton is the image architect behind some of R&B and hip-hop's most iconic acts, like Mary J. Blige, Jodeci and Lil' Kim. As Puffy's then-girlfriend in the early 1990s and stylist for many Uptown and Bad Boy artists, she freed the nipple before Instagram was even invented when she designed Lil' Kim's purple pantsuit for the 1999 MTV Video Music Awards (you know the one) and created the matching monochromatic hair and outfits for the "Crush On You" video. She crafted Mary J. Blige's "Not Gon Cry" video style, featuring black lipstick, chunky sunglasses, a Jackie O.-esque head scarf and golden twisty earrings.

In 2001, she and Harlem trailblazing atelier Dapper Dan, who invented logomania, crafted a one-of-a-kind bubble coat and complementing outerwear for Puffy, G-Dep and Black Rob in the "Let's Get It" video. After various high-fashion dustups (Fendi sued Dapper Dan for using its logo without permission; Gucci sent their own version of a Dapper Dan creation down a runway without involving him in its creation), Dapper Dan now holds an esteemed position — on his terms — in a creative partnership with Gucci, while Hylton is a Global Creative Partner at MCM, another logo-maniacal label. Her role allowed her the power to create Beyonce's "Apeshit" MCM outfit for stylist Zerina Akers, accentuating the luxury in everyday African-American style.

On matching hair to an outfit for the first time in Lil' Kim's "Crush On You" video: 

The inspiration came from The Wiz and there's a specific scene in the Emerald City where the wardrobe changes from red to yellow to green and blue. Lance "Un" Rivera was the director and he wanted to recreate the hip-hop version of that scene. I wanted to take it to the next level and not just change the clothes for Kim, but I thought that changing the hair, and creating a monochromatic look from head to toe would be fire — and it was. Dionne Alexander, another amazing creative [hair stylist] got my vision right away. At that time, people didn't wear their hair to match their clothes, so I went to the Halloween store near 14th Street [in Manhattan], got the wigs, and Dionne brought them to life. It was her, makeup artist Nzingha Gumbs and myself and we would sit down together and decide on the overall style. We were a dream team.

On creating Lil' Kim's Infamous 1999 MTV VMAs look: 

I was inspired by a conversation I had with Missy Elliott. We were hanging out at her house listening to music and talking fashion and she said, 'Kim is a bad bitch. If I was Kim, I would just have one titty out; Kim could do some shit like that.' And I was like, 'Hm, that's very interesting!' I stored that idea in my head and the next big event we had was the 1999 MTV Video Music Awards, and I brought it to life by using Indian bridal fabric doing a one-shoulder, one-piece jumpsuit; I wanted to make it really girly and beautiful to offset the fact that her breast was out. Dionne Alexander did the hair and Nzingha Gumbs did her makeup. [When Diana Ross flipped Kim's breast onstage] I was standing there like, 'Oh my God,' because the pasty was applied with eyelash glue, so I was like, 'Please, please, please!' But I was so happy that it stayed on!

On fighting for her ideas despite pushback: 

For Mary J. Blige to keep the twisty earrings on in the "Not Gon' Cry" video, that was a fight. I was told it was 'distracting' but that was because it was Black fashion. But they asked if I 'could put something smaller in her ear' and they were relentless. But I was like, 'Nope, it's fine,' and by the third time, I said, 'If I have to tell Mary, it's going to be a problem. She's not taking her earrings off and we know what that's about. It's not distracting, you don't want her to have that look that's true to who she is and it's actually what makes it authentic and speaks to her fans.' When the video came out, so many women came up to me and talked about the earrings and how that was so hot that she wore them in her music video.

Credit: CREDIT: DESIGN BY JENNA BRILLHART. IMAGES BY GETTY IMAGES, BAD BOY RECORDS, COURTESY.

Sybil Pennix

If you wore pleather outfits or Timberland boots that weren't wheat colored in the late 1990s, it was partly thanks to Sybil Pennix. As Puffy's assistant while he was an A&R executive at the now-defunct Uptown Records, Pennix became the first in-house stylist for acts like Heavy D, Mary J. Blige, Jodeci and more, before "in-house stylist" was really a thing. Uptown head Andre Harrell sent her to buy clothes for Blige like she was "shopping for your sister," and a role was born. "I grew up in the Midwest, and my inspiration came from Black people and poor white people," says Pennix. "I mixed those looks and that's what I gave Mary J. Blige." Then, when Puffy began Bad Boy Records in 1993 touting Notorious B.I.G. and later Total (the latter whom she managed), Sybil moonlighted there while remaining at Uptown, styling both rosters. Later she styled early Source and XXL magazine covers, dressing artists in a mix of luxury and round-the-way fashion with a special talent for bringing something "they'd never seen before."

On convincing heritage brands to work with rappers and R&B singers: 

In the beginning, the big fashion houses didn't let us pull sample pieces from their stores or showrooms, but I talked myself into a lot of houses. I was down with Supreme and Triple 5 Soul, we all came up together, and I'd mix that with Gucci and Prada. I used to go into Prada and pull clothes before they'd let anyone else do that, but I came from an engineering and business background so I brought that reasoning to the brands and it worked.

On bringing Timberland boots from the forest to the streets: 

Before I came, Misa and Puffy did Jodeci's first album and put them in motorcycle boots. One day, because Puffy didn't want to or know how to style a woman, Andre asked me to 'go shopping for your sister' but for Mary. I started getting her designer boots that they'd never heard of and Andre loved it. I'm the reason Jodeci started wearing leather and Timberland boots. I wrote Timberland, because they didn't want to send us boots for videos; we had to buy everything. They said their market was — they didn't say white, but they said, 'people hiking in Colorado.' And they were right, but I wrote them a note because Biggie's feet were big and I told them if he wears these boots, it'll be huge for their brand and it would explode. Brooklyn and Harlem weren't wearing the sub-below Timberlands yet, and I was always trying to find something different.

On Creating leather-in-the-desert chic: 

I put Jodeci in leather in the desert for the "I Cry For You" video, I fought Puffy tooth and nail on that. They were at the forefront with how Black artists love to wear furs, they loved it and they actually weren't hot! They wanted the leather, they said, 'Oh my God this is so different!' We took off the shirts, so they weren't that hot, which ended up becoming a great image for them. 

Credit: Design by Jenna Brillhart. Images by Kiki Peterson, Courtesy, Stephanie Angulo and Caleb & Gladys.

Kianga "Kiki Kitty" Milele

Every piece of contemporary streetwear draws on the designs Kiki scratched out as a burgeoning designer at FUBU and nearly every other urban wear brand from the early 1990s to today. After sewing gowns and party dresses for friends and family in high school, Peterson attended New York City's FIT, where she was recruited as one of the first designers at FUBU and an assistant to Sybil Pennix at Uptown Records. She soon became the creative director for FUBU Ladies, where she put superstars like Janet Jackson in the brand, before leaving to start her own brand called K.A. Kitties and freelance design for nearly every urban label, from Rocawear to Heatherette to Nicki Minaj's K-Mart line and Beyoncé's House of Dereon. Now, she's begun a resortwear brand called K. Milele. In 2020, she was featured on Netflix's Next In Fashion, an appearance that illuminated long-held racism and cultural appropriation in mainstream fashion. (Pyer Moss designer Kerby Jean-Raymond, appearing as a judge, walked out rather than send Kiki home during a streetwear challenge — something he knew she'd been at the forefront of.)

On finding her own style through a Jodeci and TLC wedding:

I was also styling at Uptown, assisting Sybil Pennix, while I was at FUBU. I styled Jodeci and T-Boz from TLC for "Love You For Life," and that was my first video set. It changed my life. Jodeci's style introduced me to a new way of rockin' shit. I was always doing my own shit randomly and making shit I felt I needed. But they gave me real fashion inspiration that was on my level. Before that experience, I'd only had Ebony and Jet magazines and they spoke to an older audience, but this was so fresh, new, fly.

On learning the fashion business from all sides: 

Working with Sybil, I helped to style Total's first album cover. It was dope because I'm learning the technical stuff in school but working with FUBU, I'm learning how to grow a business. Then at Uptown, I'm learning where the style comes from because music videos are what we look to for what's dope and how to rock shit. We want camouflage, so we go to the army-navy shop, no one's making it for us, like the Carhartt suit is a real workman's suit. I learned what streetwear is and it's exactly what it sounds like, it's what people in the community are really wearing. I saw the birth of all that, so as FUBU grew, we incorporated camouflage into our collection. We can't get it from the army and navy store, we're doing our own cut and sew, so we sent the design to the factory and they asked for our print. I was surprised they didn't have camouflage so I just drew a weird shaped print in a camouflage color and it became the FUBU camo print. The FUBU owners liked it, but I was like, 'This sucks!' It was all so fun.

On launching FUBU Ladies: 

I was begging to do women's immediately and the FUBU owners were always like, 'Next year, Kik,' but then they let me do a small 10-piece capsule collection. We did a denim-style jacket and pant made from satin that was big, and the whole collection sold out and everyone wanted more. The FUBU owners couldn't handle a whole other line so they licensed the FUBU Ladies to Jordache and I became the creative director. It was an office full of women and it was awesome! We wore everything all the time, our merchandising was on point, so buyers knew exactly what to buy because they saw how we rocked it. It was a fun, vibrant office.

Credit: Design by Jenna Brillhart. Images by Getty Images, © Janette Beckman, Alamy, Jean Messeroux (@jeanthehueman) and Courtesy.

April Walker

Today's jean suit is a staple because of April Walker's talent for listening to her customers and the marvelous ubiquity of Mary J. Blige and Method Man's "You're All I Need" video. Walker says visiting Dapper Dan at his store in Harlem in 1987 inspired her fashion career. Soon, she opened her own store in her Clinton Hill, Brooklyn neighborhood called Fashion In Effect, where she sold denim and T-shirts to fit her customers who requested lower crotches, deeper pockets and pants wide enough to fall over the top of a work boot, among other things. All of these tailoring experiences led to her own fashion line called Walker Wear, one of the first urban brands outside of early NYC lines like Karl Kani's tailored denim and the airbrush ambassadors the Shirt Kings. She boasted fans including Method Man, Notorious B.I.G., Tupac and more. But as one of the first women in urbanwear, Walker savvily kept a low profile to duck the industry sexism, and it worked. She and her team styled acts like Aaliyah and Naughty By Nature, and her line is still getting attention today. 

On Walker Wear's contrast stitching, deep pockets and wide legs: 

I was always a big workwear fan, I thought it was clean and I always wanted to make something like that, that's how Walker Wear started. We made a contrast stitching full denim suit with really big pockets and pants, inspired by the needs of the customers and it just caught on like wildfire. Everyone started asking for that suit and there was no internet at that time, so it was all word of mouth. People like Biggie, Shyne, Audio Two, who Jay-Z ran with, they all had it. Brooklyn was big but it was a small community, one person told two friends from the hustlers scene and we grew.

On the time 2Pac demanded her talents, and all Black designers, for Above the Rim:

I remember when 2Pac took me to meet the costume designer for the movie and I remember meeting Bernie Mac. And it was a big deal because he was adamant in the wardrobe trailer, like, 'I want her to style the whole movie.' And they said, 'She can't do the whole movie,' and he said, 'Well, I want all Black designers,' so that was huge.

When Method Man and Mary J. Blige made fashion history in her Rough and Rugged suit:

One of the big moments for me was Meth and Mary's "You're All I Need" video. They called and we took some product to them, and my marketing person said there was a ridiculously long line of people waiting to product place in the video, and she didn't wait and went right up to the front. They motioned her in and just took the clothes. She didn't know if he was gonna wear anything or not but it turned out he wore the jean suit. That was a really big moment because they ended up winning a Grammy, the song became an anthem, and the rest is history.

When — and why — "urban" wear became streetwear: 

Back in the early '90s, the Magic [fashion trade show] had this section called 'streetwear' and it was this intersection of Jnco meets Mossimo meets some of the urban brands. Then 'urban,' which is a code word for Black to me, got bigger and then around 2000, we started seeing brands — even Supreme which began as a skate and surf kind of brand  — start expanding their base intentionally to cater to that market. Urban fashion and streetwear are the same damn thing, it's just expanded the narrative globally and tried to reframe and remove the original starting point of how this began. 

Credit: Design by Jenna Brillhart. Images by Getty Images.

June Ambrose

Though she began her career in investment banking, June Ambrose ditched finance to join the early urban wear explosion as the marketing director at Cross Colours, the baggy, brightly hued 1990s clothing line that preached diversity and inclusion before those became hiring buzzwords. Thanks to her flamboyant style and imagination, she created singular looks like Missy Elliott's giant black blow-up suit in "The Rain," and Puffy and Ma$e's shiny suits in the Notorious B.I.G.'s "Mo Money, Mo Problems" videos. Later she encouraged Jay-Z to "Change Clothes" and wear suits, and served as creative director for Missy's Adidas collaboration.

On Cross Colors and the music industry:

When I was working with Cross Colors, it was a time when hip-hop was becoming less black-and-white and more colorful and animated. It was a time when hip-hop was moving into more of a pop space and there was an opportunity for urban brands to cross over. I joined Cross Colors as their marketing director, and through our fashion shows [where I cast supermodel Tyson Beckford in his first show], ad campaigns, product placement and creative activations, we created the urban Tommy Hilfiger. My work with Cross Colors at that time helped to illustrate hip-hop's evolution of storytelling, sound, and image.

On dressing Jay-Z, Puffy — and then the world: 

I loved seeing the impact that music videos or outrageous red carpet moments had on retail and people's everyday style. I loved how consumers would go into stores to ask for looks that I had created; young men on the street would be wearing their clothing differently after seeing Jay or Puff in a look. The imagery that I created influenced new interpretations of streetwear; some of my favorite moments were when sportswear and urbanwear took on more of a high-fashion sensibility.

On the biggest lesson of her career: 

I'd say my biggest lesson has been that comparison is the biggest creative killjoy. When I was coming up, there was no Instagram; we pulled references from libraries, magazines, and our own imagination! Comparison is not only a distraction but it stops you in your tracks. You should find the space that feels most organic and authentic to your creative spirit. 

Credit: Design by Jenna Brillhart. Images by Getty Images and Courtesy of Gucci.

Bevy Smith

Bevy Smith has probably been a fly girl since birth and this born-and-raised Harlemite is the pied piper of teaching luxury brands the power of the Black dollar. She brought her flair to a career in publishing where she was a fashion advertising executive at VIBE magazine and is credited with enticing European fashion houses to advertise with Black and brown consumers and recognize the value of urban style and urban wear, which has now been retitled streetwear, much to Bevy's chagrin. Now, Smith hosts "Bevelations" on Sirius radio after stints on Page Six TV and Bravo's Fashion Queens, and has just released her book, Bevelations: Lessons From A Mutha, Auntie, Bestie.

On landing VIBE's first luxury fashion advertising client: 

I started pitching fashion houses for VIBE in 1998, and I remember the white guy I replaced said, 'Oh, they'll never talk to you. They don't even take my calls, so they'll never talk to you.' Gucci was my first selection because growing up near Dapper Dan's shop in Harlem, I saw what he did with logomania before anyone else. Brands were not even using their logos in that way; Dap started that. A lot of people don't realize that then Gucci was down on their heels, and when they gave it to Tom Ford [who became creative director in 1994], he revitalized the whole brand. I won't say [getting their business] was easy but I remember Tom Ford in WWD said something like, 'I made this collection for Whitney Houston if she married a hip-hop star and they were vacationing on a yacht.' I knew then that Tom knew Black people are fashionable, we set trends. So I had that quote laminated and put together some of the most iconic looks that Emil Wilbekin, the fashion director at that time, had ever styled using Gucci clothes, put it all in a beautiful leather box and sent it to Gucci. Then I got a meeting, and it was good but I didn't get their business at first. But the next summer, we got two pages [of ads in the magazine]. Then Prada came into the book with 10 pages and that was ground-breaking.

Teaching luxury houses the value of the Black & Brown dollar, through American history:

They said the VIBE consumer household income didn't match Vogue or GQ but a part of our cultural DNA is looking good. That's not to peacock, that's literally for our own safety, to work, get a taxi, the basics. When I pitched in Europe, I gave them the information behind our demographic, about why we wanted to look good and why we were just like white Americans. This country is built on materialism and moving on up and people living above their means, so we were really no different than the average American. It's just that when we do it, it's looked down upon. We needed to look good to get work and even be accepted into stores. I'd give full-on history lessons about the Jim Crow south and Reconstruction. During Reconstruction, the KKK spread rumors that we were not only lazy, but dirty and unkempt, that's why to this day, we over-index in consuming personal hygiene products compared to our white counterparts. I believe that's because of the stigma that was placed on us hundreds of years ago. Puffy, Lil' Kim, Mary J. Blige, this wasn't a fad, this is legacy — and that's when I would take out James Van Der Zee's Harlem Renaissance photos.

Why streetwear is just urban wear with a markup: 

Streetwear is the white version of urban wear, like what Supreme and Virgil Abloh does with Vuitton. We never called our clothes anything, outside of Andre Harrell, who coined the phrase "ghetto fabulous." We create something, then they copy it and put their designer label on it and now you're paying $1,000 for something you could get on 125th Street? Before Dapper Dan, no one thought to put monograms on clothes. People know that he took designer clothes and put them on urban silhouettes, but what people don't get is that brands were not even utilizing their logos in that way. So when Marc Jacobs at Louis Vuitton or Tom Ford at Gucci did it, it was such a major moment in fashion because that was cribbed from Dapper Dan. And at this point, Dap had been forced into hiding for trademark infringement and they're taking literally what he's been demonized for and putting it on the runway and selling it in stores. Ain't that about a bitch? It burns my biscuits. 

Now that we've got history straight, let's get present-tense: 

Gucci began a creative partnership with Dapper Dan in 2018 and the two brands work collectively to bring his designs to the masses, which is full circle from when they sent then-Fendi corporate lawyer, now Supreme Court Justice Sonia Sotomayor to serve a cease-and-desist order in 1992. Walker (quoted in the graphic above), recently restarted Walker Wear with one of her original supporters, Method Man, as a model. Ambrose is creative director at Puma. Peterson is ramping up her resort wear brand K. Milele, and Smith has released a book entitled "Bevelations," full of her colorful musings. Just like Black resilience despite America's sordid racist history, the cultural guards continue to elevate and now, finally, receive recognition and financial reciprocity for their genius — which is exactly the way it should be.

Whether fashion, beauty, or culture at large, the arts in America have one commonality keeping them afloat: Black creativity and excellence. In this package, called State of the Arts, we examine the leaders — those unsung background players and celebrated 'firsts' — who are the best at what they do. The state of the arts? We'd have to say they've never been better.