Behind the Music: June Ambrose on Hip Hop’s Most Iconic ’90s Videos

June Ambrose, the stylist behind some of the most memorable looks in the heyday of rap, offers a rare look at how those outrageous choices came about.

June Ambrose

With clients and collaborators like a young Jay Z and Missy Elliott, June Ambrose was responsible for styling many of the most iconic videos in ’90s hip-hop. Working with the director Hype Williams, rap’s own Edith Head dreamed up new characters and outfitted artists in exaggerated, influential styles that drew inspiration from across eras, social classes, cultures, and musical genres.

Though music videos of the period might be likened to short films in execution, their budgets approached the sums allotted to generously funded indie productions. Ambrose recalled making Busta Rhymes and Janet Jackson’s “What’s It Gonna Be?!” video for as much as $4 million. (For comparison, documents obtained by a Beyoncé fan site estimate the budget for Lemonade at $1.35 million—and that’s still a lot.)

“It was artist development,” she said. “It was character development.” Musicians like R. Kelly, Will Smith, and Missy Elliott inhabited new worlds and invented personae that could be cast off with their garments at the end of a shoot. Here’s the story behind some of the best looks of hip-hop’s music video heyday.

R. Kelly, “Half on a Baby,” 1998: Ambrose worked with R. Kelly for many years, though they parted ways “for my spirit and soul,” she said. “A lot of stuff that went on behind the scenes … I just couldn’t witness anymore.” But before it all fell apart, Ambrose styled some of Kelly’s most involved and iconic looks. For “Half on a Baby,” Kelly’s silk pajamas seemingly dissolve off his body about three-quarters of the way through the video. “When he’s walking up the steps,” Ambrose explained, “the suit is flying off his body, and I had like six assistants on the side pulling the strings.” It required about 15 takes to get it right — and 15 silk pajamas for Ambrose to sew.

Missy Elliott, “The Rain (Supa Dupa Fly), ” 1997: “In the treatment, [Hype] was like, ‘She’s a Michelin Man,'” Ambrose recalled — but she refused to dress Elliott in a white suit. “My whole thing was like, big glasses and shiny suits,” she said. Ambrose countered Williams’s proposal with an offer of patent leather and vinyl, but it was Williams who dug up the vintage Alain Mikli fire-flame glasses (“very rare, very expensive”) that complete the look. With Williams’s go-ahead, Ambrose designed the suit herself. But having never built an inflatable costume before, she found it kept deflating. It turned out there was a tiny leak that they hadn’t discovered till the team tried to inflate Elliott at a local gas station. “As we were walking back down the street to the set,” she said, “the suit is slowly, slowly, slowly deflating.” It worked to their advantage — Elliott needed a bit of room to dance, which would have been impossible if the suit were structurally sound, as intended. Ambrose ran out to grab a bicycle pump just before the shoot and worked with the choreographer to maneuver a quick air refill into the shot. “I’m behind the suit in the entire video pumping air back into it, per pop-lock,” she said. But as many times as you watch “The Rain (Supa Dupa Fly),” you won’t find Ambrose anywhere in sight.

Will Smith, “Gettin’ Jiggy With It,” 1997: Ambrose worked with Hype Williams yet again for Will Smith’s “Gettin’ Jiggy With It.” Their trademarks are both readily apparent, between Smith’s shiny bomber jacket and the distorted fish-eye camera angle. “Hype was constantly coming up with the most outrageous things,” Ambrose said. “I really give him a whole lot of credit for being the change agent at the time, because without those treatments, we really wouldn’t have had the script, in a sense, to do what we were doing — to tell the story.”

Foxy Brown and Jay-Z, “I’ll Be,” 1996: At the same time as Missy Elliott broke the mold for women in hip hop in the ’90s, Foxy Brown profited from the status quo. “That was her marketing strategy, talking about how ill her vagina was,” Ambrose said. “I was still trying to put her in a Norma Kamali one-strap dress, but it had to be super tight, and I was able to get it to the floor, but it had to be body con.” One of the resulting outfits in Brown’s Jay-Z collaboration “I’ll Be,” directed by Brett Ratner, does skim the floor as she raps “drippin’ Gabbana,” albeit with oblique-baring cutouts.

Jay-Z, “Feelin’ It,” 1997: Jay-Z’s “Feelin’ It” video was shot in Jamaica. Ambrose said she courted Armani to provide Jay-Z’s suits for the video, but as late as 1997 she still wasn’t able to recruit high-fashion designers to outfit her musicians. So she made the suit herself. “I wanted Armani first because I liked the softness of the shoulders,” she explained. “He wasn’t a suit guy, but I wanted him to feel like he was wearing a jogging suit while he was wearing his Armani suit.”

The Isley Brothers and R. Kelly, “Contagious,” 2001: In the videos for “Contagious,” by the Isley Brothers featuring R. Kelly, and for “Down Low (Nobody Has To Know)” by R. Kelly featuring the Isley Brothers, Ron Isley plays a fictional mob boss named Mr. Biggs. “Ron Isley’s no gangster,” Ambrose said. “It wasn’t always about gangsta music being real, but then you were storytelling and exaggerating certain things.” Rather than drawing from the gang culture of inner cities, Ambrose said she was inspired by “all of these great iconic movie references,” like Al Capone, the zoot suit, and the oversized gold medallion.

Puffy Daddy, Mase, and the Notorious B.I.G., “Mo Money Mo Problems,” 1998: The second single off B.I.G.’s album Life After Death, “Mo Money Mo Problems” was released posthumously. “We were burying gangsta music, in a sense,” Ambrose said. “B.I.G. had just died, and this album was, you know, we had collaborations with Sting. It was like the crossover of pop culture with hip hop, so it was slowly becoming hip-pop culture.” Puff Daddy and Mase were initially resistant to the shiny suits Ambrose conceived for the video, she explained. “They were like, ‘No way. This is not hip hop.'” Perhaps not — Ambrose was inspired by carnivals, thus the shiny fabric — but she convinced her clients. “I said, ‘There are no rules. You break rules; I break rules,'” she recalled. The video was a watershed moment; the year after Ambrose started filling her styles with shiny, plastic-covered nylon, Dolce & Gabbana sent models wearing that same material down the runway.

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21 Moments That Defined 1990s Fashion

At his Spring 1993 show for Perry Ellis, Marc Jacobs sent out flannel shirts and skirts, baggy pants, floral dresses, and skull caps that led to his now-infamous firing. However, grunge became fashion — and it was okay to wrap your old plaid button down around your waist and pair sneakers with dresses. Here, Marc Jacobs fitting a model backstage before she hit the runway.

Photo by Kyle Ericksen.

Christy! Naomi! Linda! Cindy! Claudia! These models were the firsts to be household names and to this day are beauties that continue to inspire future generations. Here, Christy Turlington and Naomi Campbell at a benefit for Gianni Versace.

Photo by Jim Smeal/WireImage.

Tom Ford was hired at Gucci in 1990, and was promoted to creative director in 1994. At his March 1995 show, he sent out the top girls of the time — like Shalom Harlow and Amber Valetta — in velvet hip-hugging pants, satin shirting in jewel tones. The previously snoozy fashion house was shaken up and it was all of a sudden a sexy, jet-set brand that everyone wanted to wear, including Madonna. A few months later after the collection debuted, the singer wore one of Ford’s best looks from the collection to the MTV Video Music awards. Here, the opening look of his Fall ’95 show.

Photo by Getty Images.

Off the runways, it was Britney Spears who was making a big impact on fashion at large. Spears released “…Baby One More Time” in 1998 and suddenly every teenage girl (as well as plenty of adult women) in America was rocking thigh high socks, braided pigtails, and pleated, school girl miniskirts.

Photo by Brenda Chase/Online USA, Inc.

Ah, those good old days of the “A&F Quarterly” catalogues full of glossy, young football studs and cheerleaders in little to no clothing. There was the occasional appearance of a crinkled plaid button down shirt or a pair of barely-there denim cut-offs, but it was the overall lifestyle teens everywhere bought into. ’90s fashion will forever be stamped with a big, bold A&F logo.

Photo by David Pomponio/FilmMagic for Paul Wilmot Communications.

Galliano catapulted to fashion stardom with his groundbreaking Fall 1994 collection. With the help of important friends like Amanda Harlech, Stephen Jones, and Portuguese socialite São Schlumberger. he pulled together an East-meets-West collection that landed him at the helm of Givenchy a year later. In 1996, he then took over at Dior and put on some of the most extravagant shows the house had ever seen.

Photo by Getty Images.

Speaking of Galliano: At the 69th Annual Academy Awards in 1997, Nicole Kidman would forever change red carpet dressing by sporting one of his designs for Dior, a flawless, devastating silk gown in iridescent chartreuse that immediately appalled Joan Rivers and upstaged Tom Cruise.

The designer was the most exciting designer coming out of the London scene and he was also the most controversial. “Highland Rape,” his Fall 1995 collection, featured models clad in torn plaids lace, and also the “bumster” — an extremely low cut pant, as McQueen found the most sensual part of a woman’s body to be the end of her spine. Here, a bumster look from that collection. The introduction of this silhouette on McQueen’s runway may be the reason why the extremely low-rise look was so popular in the early 2000s.

Photo by Rose Hartman/Getty Images.

Angela Chase in My So-Called Life, Cher Horowitz in Clueless, Liv Tyler’s Corey in Empire Records, Winona’s Lelaina Pierce in Reality Bites, Sofia Coppola’s girls in The Virgin Suicides — all characters who’s on screen style has influenced what every girl of the ’90s (and today!) wanted to wear.

Photo by Paramount Pictures/Getty Images.

The signature, upside down triangle Guess logo was positively ubiquitous in the ’90s. Guys and gals alike were enamored by the sportswear brand’s jeans, overalls, and logo t-shirts. Today, it feels as relevant as ever, with top models like Gigi Hadid fronting its recent ad campaigns and rapper A$AP Rocky as a collaborator.

Photo by Al Freni/The LIFE Images Collection/Getty Images.

We all know the story, the English waif who changed fashion, rushing in this so-called heroin chic look. She was the face of Calvin Klein Obsession in the early ’90s, and here, she appears with the designer in 1995.

Photo by Ke.Mazur/WireImage.

Paltrow stepped onto the 1996 Academy Awards red carpet wearing that now- iconic pale pink Calvin Klein slip dress and the best accessory one could ask for: Brad Pitt on her arm. We’ve been looking for a slip dress this good ever since.

Photo by Barry King/WireImage.

There was Marc Jacobs, Calvin Klein, Tom Ford, and Alexander McQueen, and then there was Helmut Lang. The designer, who left the scene in 2005, changed fashion forever with his minimalist, utilitarian designs. His influence is still widely present in the work of many top contemporary designers of today.

Photo by Getty Images.

The hair, the slip dresses, those ’90s light-washed jeans that we’re all coveting today — Winona was the ultimate ’90s It girl with an edge. Liv Tyler, in Empire Records, is a close second.

Photo by Max B. Miller/Archive Photos/Getty Images.

Winona might have been the quintessential It girl, but Parker Posey’s Mary in Party Girl was the dreamboat socialite of the downtown, a precursor, in style and personality, to all the party girls who followed, from Chloe Sevigny to Paris Hilton. Photo courtesy the Everett Collection.

Those oversize logo T-shirts and sweatshirts, the briefs with the Tommy Hilfiger logo peeking out of jeans, and the big Hilfiger logo duffel bags — the brand was everything in the ’90s thanks to the late Aaliyah, who became the face of Tommy Jeans.

Photo by KMazur/WireImage.

You can’t talk ‘90s fashion without mentioning the Spice Girls. The all-female, British group was formed in 1994 and quickly rose to global mega stardom. Their pop-y ballads were undoubtedly catchy, but what we remember most was their platform shoes, skintight leather mini dresses, and sequined getups. Perhaps most importantly, this was the beginning of Posh Spice, aka Victoria Beckham.

Photo by Tim Mosenfelder/ImageDirect.

It was in 1993 that America learned of one Björk Guðmundsdóttir, best known simply as Björk. With songs like Venus as a Boy and Big Time Sensuality, her seductive interpretation of triphop, and her defiant androgyny, she came to define the style and look of the European alternative scene, one that Madonna herself, the decade’s earlier provocateur, would crip when she asked the Icelandic singer to collaborate on her Bedtime Stories album. Here, she is pictured in 1993 in The Face, one of the iconic magazines of the period like Details and Sky that is no longer around. Photograph by Glen Luchford.

The famously reclusive Martin Margiela most certainly earned his space in the’ 90s fashion history books. Like Lang, the Belgian helped reinvent the codes of fashion with his provocative, trompe l’oeil signature designs. Few collections better embody all things Margiela better than his Spring 1996 collection, which included that sequin print dress and nude bodysuits.

Photo by Karl Prouse/Catwalking/Getty Images.

In 1995, Isaac Mizrahi became a cult figure. Yes, he was already a rising star in the world of fashion, but a little documentary called Unzipped would make him a household name. After a badly reviewed collection, he allowed his then partner Douglas Keeve to follow him around as he put together his fall 1994 collection. As the legendary Polly Mellen pointed out in one scene, “It erases EVERYTHING.”

Photo by Nick Waplington.

After Sex and the City launched in the late ’90s and fan girl Carrie Bradshaw cemented Manolo Blahnik as the shoe to be wearing, the footwear brand was catapulted to cult obsession status. That was only further cemented in the Sex and the City movie, when Big asks Carrie to marry him with a pair of blue Manolos.

Photo by Getty Images.