June Ambrose & Misa Hylton: The Women Behind Hip-Hop's Greatest Fashion Moments
The evolution of styling in hip-hop mirrors the trajectory of the genre itself. In the beginning, there was not a specific title appointed to the person tasked with defining the visual language of an artist. Many critiqued rap as something that would not last for a significant period of time, therefore it was not always given its due diligence. As the genre gained popularity, so did the need to recognize the style architects behind the look of rap’s elite. Consider the work of Harlem couturier Dapper Dan: the man who created custom designer pieces for the likes of Salt-n-Pepa and Eric B and Rakim in the late 80s and recently partnered with Gucci to create a capsule collection reminiscent of his original designs. While Dapper Dan represents a period in the music industry where artists were creating work for the appreciation and respect of one another, two women in the 90s helped to usher in the next wave of transition. The styling work of June Ambrose and Misa Hylton solidified many of the biggest names in hip-hop as bona fide stars by crafting a strong identity that reflected the innovation in their music.
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Between these two stylists, Ambrose and Hylton are responsible for a majority of the oft-copied fashion moments of the late 90s. They each began their styling careers interning at Uptown Records during the time when Sean “Diddy” Combs made the transition from intern to A & R at the label. His new role afforded him the chance to develop the sound of newcomers including R&B group Jodeci and a teenage Mary J Blige. Image represented an important part of this development, creating a “right place, right time” opportunity for Ambrose and Hylton to contribute to the start of a new dawning in music. Hip-hop’s transition from an experimental form of expression to popular music became lucrative in the late 90s, due in large part to its visual appeal. Throughout their careers, both stylists put together (and, in some cases, custom designed) iconic looks for the likes of Missy Elliot, Jay Z, Foxy Brown, Usher and Lil Kim.
When considering the origins of hip-hop, style factored into the equation heavily. The bold sound of rap required an equally bold look to match, one that mixed urban comfort with a healthy dose of braggadocio. The 90s saw rap leave its neighborhood setting and enter the global arena. The genre consistently rode the fine line between familiarity in the present and aspiration for what was to come. Clothing became a part of the performance, a necessary element that brought the artist’s persona full circle. And though the genre seemed to bend more towards a masculine bravado, female MCs in the 90s were able to use their wardrobes to carve out new lanes for themselves.
One of the most notable of these MCs is Missy Elliot. The Virginia-raised rapper introduced a futuristic sound to hip-hop with her first solo single “The Rain” in 1997. In an interview that same year with writer Hilton Als for the New Yorker, Elliot commented that she wanted her work to show “where black folks are from, and where we’re going.” The Hype Williams-directed video for the song did just that. The look that is most synonymous with the song is also its most outrageous: the video opens with Elliot sporting her signature finger waves while wearing a voluminous black patent leather jumpsuit with black ombre lipstick, hoop earrings and red sunglasses affixed to a rhinestone-encrusted headpiece. Williams’ trademark style of shooting through a fisheye lens helped to exaggerate the extremity of the suit (the piece actually had a leak in it, which ended up being better for movement.) The video represented a defining moment in Elliot’s career—she set herself apart as a female rapper who eschewed the seductive route in order to offer an alternative to the predominant media representation of women. It also became the start of a creative partnership between Williams and the video’s stylist-both of them would go on to work on the video for Elliot’s next single “Sock it 2 Me.” The name of that stylist was June Ambrose.
Ambrose’s fashion career began in an unlikely place: investment banking. During her stint in this field, she came to realize that her passion lied in more creative endeavors. A friend set her up with the internship at Uptown where she worked her way up through careful observation and an open mind. While she originally did not know what being a stylist entailed, her first official gig as such was in 1990 when she put together looks for a local DJ signed to the label. She would go on to open her styling company Mode Squad a few years later and, in 1997, landed the opportunity to style videos for “The Rain” and Biggie’s posthumous “Mo’ Money Mo’ Problems” single. Both ventures put her talents well on display. Ambrose has a penchant for shock value: she recognizes when a major moment is occurring and is not afraid to take a chance on what she believes in. For “Mo’ Money Mo’ Problems,” that meant convincing Williams, Diddy, and Harlem rapper Ma$e that red shiny suits were the way to go. Her choice in material grew out of her West Indian heritage and outfits worn for carnival-by applying an unexpected fabric to the baggy silhouette that prevailed at the time, Ambrose achieved a fresh look that built upon the past, announcing hip-hop’s dominance and innovation in the pop landscape.
Misa Hylton’s opportunity to style came through R&B group Jodeci. The look for R&B singers at the time was polished in order to match silky smooth vocals: suits, hard-bottomed dress shoes and minimal accessories. Working with Diddy on image development for the act, the pair decided to go in a new direction by outfitting the group in combat boots and baggy pants. The change took major convincing from the label as execs were not sure that the look would sell, but the move proved to be successful for Hylton as she was given the chance to do a similar style with Mary J Blige’s video for “Real Love.” In an interview with Hot 97, Hylton commented that Blige’s “magic wasn’t in a ball gown—it came in a different way.” Blige’s music often told of the complex emotions that come with love, whether falling in or out of it. She would become known as the queen of hip-hop soul and her look at the beginning of her career reflected this moniker: while she poured her heart out in a song, she wore backwards baseball caps, oversized jerseys and Doc Martens. Rapper Lil Kim later referenced the look as “chic gangstress.” The style became a hallmark for Hylton: her work consistently shatters expectations of what can and cannot be done in certain spaces. She continued this in the styling for the music video “Not Gon Cry.” The song was featured on the soundtrack for the hit movie Waiting to Exhale, which focused on the complicated relationships four women had with the men in their lives and their friendship with one another. The video served as another case where Hylton had to stand firm in the wardrobe she envisioned, which she went on to describe as a “ghetto fabulous Jackie O”: black leather, dark sunglasses, black lipstick, and gold hoop earrings. The look was in stark contrast to the neutral serenity of the movie’s setting in the Arizona desert.
Hylton’s most iconic work stems from her collaborations with Lil Kim. She is the mastermind behind two looks in particular: she styled the “Crush on You” video and the infamous lavender one-shoulder jumpsuit that Kim wore to the MTV Video Awards. While there are plenty of legendary ensembles to dissect throughout Kim’s career, these two stand out because they highlighted a shift in Kim’s trajectory. Hylton noted that "Crush on You" solidified Kim as an international star and continues to serve as inspiration for a new generation. A major reference point for the video was The Wiz, a new take on the Wizard of Oz which starred Diana Ross and Michael Jackson. Lance “UN” Rivera, the video’s director, wanted multiple scenes each set in a different primary color. Hylton’s first reaction was to play with colored wigs for each monochrome look; the video emphasized Kim as a style chameleon. Her look for the MTV Video Awards offered a fresh perspective on that theme: Hylton designed the piece using Indian bridal fabric in a light purple hue to soften up Kim’s look following "Crush on You." The jumpsuit was actually conceived from a conversation Hylton had with Missy Elliot, where Elliot said that if she was Kim, her next move would be to show up to an event with one breast showing. The look shocked the world as it was an extremely risky move, especially considering that Kim’s delicate bejeweled pasty was held in place with the same glue that is used to attach false eyelashes and hair weaves.
A similar theme throughout both stylists’ work is the idea of accessibility mixed with aspiration. It involves a remixing of a piece or label that the public is used to seeing, but elevating it in such a way that new desires are birthed. Take for example the cover of Missy Elliot’s "Under Construction" album. Misa Hylton styled Elliot in items that could be found at a local mall: dark denim jeans, pink and white Nike sneakers, a white tee and a pink bucket hat. The hero piece was the custom pink jacket with fur trim that Hylton commissioned from Dapper Dan. The jacket was exclusive, but unlike items presented on a designer runway, still attainable—a version of it could certainly be bought at a neighborhood retailer. Hylton has often described how at the beginning of her career, many showrooms would not lend her clothing because they were not familiar with rap and felt that the artists she dressed were not established enough. This forced her to get creative; she seized the opportunity to design fashion she wanted to see, fashion that represented an elevated version of her reality. In this, she followed in the footsteps of Dapper Dan. Her industrious attitude towards style set trends while highlighting street culture as a viable source of inspiration.
The impact of June Ambrose’s and Misa Hylton’s contributions to the entertainment industry can still be felt today. One of the best examples is through their work on Beyonce and Jay-Z’s video for "Apesh*t". The super-secretive project saw Ambrose styling Jay-Z in a variety of designer double-breasted suits, with Beyonce wearing a plethora of looks, including a custom MCM outfit designed by Hylton. The collaboration came about after Beyonce’s stylist, Zerina Ackers, came across a custom MCM jacket Hylton had recently designed for rap legend Big Daddy Kane. The moment represents a culmination of what the two stylists have been doing since the beginning of their careers: giving hip-hop culture the spotlight it deserves. Ambrose began styling Jay-Z midway into his career and is responsible for transforming his wardrobe into one that reflected the transition he made from a hustling rapper into a billionaire mogul.
Each stylist has gone on to expand their repertoires beyond styling music videos: Ambrose ventured into costume design for the cult classic film Belly and developed her own collections for Selima Optique and HSN, while Hylton founded her own styling school and styled runway shows for brands including Baby Phat. Hylton is also the subject of a new documentary by MCM titled "The Remix: Hip Hop x Fashion” which was screened at this year’s Tribeca Film Festival. Hylton and Ambrose’s work is legendary because it considers the ability image has to punctuate one’s endeavors. They go beyond simply dressing talent to collaborating with their clients on a variety of projects that allow them to shift roles. Although they started when the term “stylist” was not explicitly used, their careers have offered a blueprint to a new generation of stylists including Ackers, Ade Samuel, and Fatima B. When words aren’t enough, the style choices of Ambrose and Hylton consistently show that what we wear has the power to shift both our individual narratives and the culture at large.