Misa Hylton Championed Hip-Hop Style in the '90s: Now She's Got a New Mission

Missy Elliott, 2015
Ruven Afanador

Missy Elliott photographed on Nov. 6, 2015 at Root Drive-In Studio in New York City.

Misa Hylton was only 17-years-old and still in high school when, with the help of her then-boyfriend, A&R intern Sean Combs (he had yet to go by the monkier P. Diddy, Puff Daddy or Diddy) she began styling emerging Hip-Hop acts. Fast forward almost two decades later, and the Mount Vernon, NY native, who had a son with Diddy, has become wholly responsible for dressing some of the most influential Hip-Hop artists of the 90s, creating lasting, iconic music moments like Lil Kim's legendary 1999 MTV VMAs performance and Mary J Blige's "Not Gon Cry" music video. She's worked with everyone from Missy Elliott and Foxy Brown for her "I'll Be" music video to 50 Cent, Fat Joe, Remy Ma, Faith Evans, Terrence Howard and LaLa Anthony. 

Billboard Style spoke with Hylton to get her thoughts on styling, fashion and the state of Hip-Hop icons today.

Jeff Kravitz/FilmMagic, Inc
Lil' Kim during The 1999 Source Hip-Hop Music Awards in Los Angeles. 

Tell us about your first big styling gig. Who was it with and how did it happen? 

It was with Jodeci and happened because of a "right place, right time" situation. My boyfriend at the time was Sean Combs (aka P. Diddy), who was an intern when we met and had just got promoted to A&R. I was there as he was working with the group and shaping their album. I was able to help him work on the image and to sell it to Andre Harrell. At that time, the look for R&B singers were hard bottom shoes and suits, but we had what was then considered a crazy idea: to put these singers in leather, combat boots, hoodies and baseball caps that were turned backwards. Andre immediately said "hell no," but after about two hours of going back and forth, we convinced him to give us this opportunity, and after this transformation Jodeci's career catapulted. Andre came back to me with another opportunity, this time a female solo artist, and he thought we'd work great together since I was from Mount Vernon, NY and she was from Yonkers, NY. Her name was Mary J. Blige.

So what was pulling clothes for her like?

With Mary's first album it was almost impossible, and at first it was really difficult to get into showrooms. I felt a lot of discrimination at that time and we were all very young. People would like at us like, "who are these kids and what is going on?", but after that it was easy. When I started working with Lil Kim, she was so little (4'11 and size 4-½ in shoes) and by that time even though I had access, nothing fit her. She wore like kids size 11 or 12, which is how I got into designing. 

Can you describe what it was like to work with Lil Kim?

Working with Kim really allowed me to get into my creative bag. She's such a sweetheart, she loves to do things that are out of the box, she loves to stand out and she loves fashion. When you talk about changing hair colors and the videos, you really can't push creativity further than that, especially at that time. Today, everyone is walking around with a different wig in different colors. But that wasn't normal back then and to do her "Crush On You" video was a big time risk. People were telling us we shouldn't do it, but I stood my ground and the director, Lance “ UN “ Rivera, backed me up. We created a masterpiece and that's when Lil Kim made her crossover to MTV. "Crush On You" was actually inspired by "The Wiz," which featured Michael Jackson, Diana Ross and so many others, and it was after that video that her career really took off.

What was your driving force for becoming a stylist back then and what does your inspiration and styling process look like now? 

The driving force for me was passion, and I had a passion for exploring my creative side. I also had a passion for fashion. I know how corny that sounds but I love clothing and everything about [creating an] image. Back then being a fashion stylist wasn't a career choice; I had no idea what to do or how to do it. It honestly came very naturally as I was a very eclectic and creative child; however my parents weren't familiar with that world and didn't see that as a valuable career.

For me, inspiration comes from everywhere and starts as a daydream. When I was a pre-teen, the radio only played Hip-Hop on Fridays and Saturdays and was hosted by Mr. Magic & Kool DJ Red Alert. I would sit on the floor by the radio with my cassette tapes and record the music and while listening I envisioned wardrobe. There weren't many visuals out at that time; basically, there were none. So you had to sit and imagine what these rappers looked like, what they should wear, what I would wear, and what my friends would wear.

Ruven Afanador
Missy Elliott photographed on Nov. 6, 2015 at Root Drive-In Studio in New York City.

Favorite brands to pull from?

I love all brands, but if I ever had to single one out it would definitely be Versace. What Gianni & Donatella Versace were able to build as far as meshing music and fashion is incredible, and the way they embraced [a black model like] Naomi Campbell back then was just unheard of. As a creative and designer, I just think he is so amazing. 

?Do you have any style icons?

No, I don't have any style icons.

Excluding Rihanna, which celebrities do you think have the best style today?

Teyana Taylor, Lana Del Rey, and Andra Day. But there's really not a lot out there; things are so cookie-cutter and in my era that would've never been the case. It was all about being unique and doing something different. We wouldn't dare wear what someone else wore, and definitely not for show time.

You have your own styling academy, Misa Hylton Fashion Academy (MHFA). Tell us a little bit about that. 

MHFA was launched in 2012 along with my co-founder, Jai Hudson, who's also a stylist, author and celebrity designer. It all started as an idea to give back to my styling community. As a mentor, mother and teacher at heart I saw there was a void. An exciting career as a "stylist" is available these days, but no one is really preparing and passing down the knowledge and skill set needed to turn this opportunity into a reality. We also teach the students that there are different realms of styling, from celebrity, editorial, costume design, to television and film. The program lasts for about 12 months and students leave with the knowledge, skill set, business exposure and etiquette that you need.

Can you share any current projects you're working on?

I just finished styling a commercial with Honda that takes you through different eras of fashion and the cars of each era. I'm also currently working with FUBU on a campaign; as you know, they're on the verge of making a comeback.