On Tuesday night, Nicki Minaj arrived at the TIME 100 Gala, head-to-toe in Givenchy and arm-in-arm with the house's designer, Riccardo Tisci, who seemed to be positively giddy to be her date. LOOK WHO I TOOK TO THE PROM, Tisci said on Instagram, even if some would argue it was Minaj who took him.

Once upon a time, however, the biggest stars in hip-hop could not even attract the attention of elite fashion designers, much less act as their muses. When the genre’s great videos began to emerge in the ’90s, designers simply didn’t value hip-hop’s cultural capital, according to the legendary stylist June Ambrose. The music video icon worked with Missy Elliott and Jay Z throughout the ’90s, and on pretty much every Hype Williams-directed video of the era—not to mention Belly, the 1998 movie he wrote and directed starring Nas and DMX, which has gone on to become a cult classic and one of the totemic artifacts of that era of rap.

Ambrose, 44, studied costume design before a brief stint in finance. She began a job in marketing at Uptown/MCA Records just as Puff Daddy embarked on his A&R career around 1992. Before long, she was working with Will Smith, R. Kelly, and long-time client Jay Z.

“Because designers wouldn’t give us clothes,” she recalled, “I started not just styling the music videos but designing the costumes that I saw in my head.”

Take, for example, Jay Z’s soft-shouldered suits for his 1996 video “Feelin’ It,” a languid cruise off the Jamaican coast. Ambrose couldn’t get Armani for the video, so she designed a starter suit for the rapper, who, at that point, was mostly accustomed to tracksuits. As hip-hop’s cultural cachet increased, Ambrose was eventually able to get Armani for him, as well as Ralph Lauren and, as Jay Z matured from rapper to rapper-mogul, Tom Ford. It seems to suit him just fine: His 2013 album features an ode to the designer entitled, predictably, “Tom Ford.”

“That felt like his armor,” she said. “That was probably the strongest shoulder we’d ever experienced. He was ready for it. He was standing up, his shoulders were pushed back.” She experimented with fit, trying out Dior’s shortened silhouettes, and with accessories, putting the rapper in ties with classic double-Windsor knots.

Fashion houses began to take note: In 1997, Ambrose brought her trademark plastic-covered nylon jumpsuits to Puff Daddy and Mase’s “Mo Money Mo Problems” video. The following year, she recalled, Dolce & Gabbana sent its models down the runway in the same material.

“Europe started to recognize that we could do high fashion,” she said, alluding to the racial homogeneity of the industry. “Costume design was not to segregate the culture. It was to say to those designers that we inspire a culture, not only in music but at retail.”

It has worked both ways. Just as couture garments have worked their way off the runway and onto the biggest stars in hip-hop, ’90s streetwear has earned its own modicum of respect, making its way back into the annals of high fashion—look no further than recent collections by Alexander Wang, Puma x Fenty by Rihanna, and Off-White for evidence. In a hybrid of the two phenomena, Drake performed in 2011 in a black velour Versace tracksuit.

Women like Elliott also offered a counterpoint to the hyper-sexualized stereotype of women in hip-hop at the time. In her debut video, 1997's “The Rain (Supa Dupa Fly),” Elliott appears alternately in an inflated black vinyl suit, a red raincoat, and yellow track shorts with a matching yellow jacket. There was not a bikini or fur in sight.

“It was … liberating to women who didn't have the typical, stereotypical looks of a woman in hip-hop,” Ambrose said. “They were objectified—and I turned Missy into a cartoon character.” She laughed at this. “Missy was very shy, so this was a great way of her getting into character and having fun with it, and not feeling the pressure of what the industry had put on women at the time in music.”

Not that Ambrose didn't play within those gendered roles. She worked with Foxy Brown during the Ill Na Na period, when Brown's marketing strategy hinged on selling sex. In many ways, it parallels the current mood in hip-hop. "With the provocativeness of the new bodies and butts, it’s actually on steroids right now,” Ambrose said.

But her work with Elliott showed that it didn’t have to be so. Together, they also landed a deal with Adidas for Elliott’s “Respect Me” collection in 2004, one of the first collaborations between a brand and a hip-hop star. Its echoes are felt even today: Jay Z collaborated with Barneys in 2013; Kanye West joined forces with A.P.C. even as Yeezy came into the world; A$AP Rocky made Guess happen all over again and Pharrell has reignited G-Star Raw. This crossover between fashion and hip-hop also laid the groundwork for Diddy's Sean John and Jay Z’s own Rocawear, both launched in 1999.

Just look at Beyoncé's album-length video “Lemonade,” a paean to the black female experience in America. In it, she wears Roberto Cavalli, Hood By Air, Yeezy, Nicolas Jebran, Gucci, more Gucci, and Givenchy. On Instagram, each designer on that list scrambled to take credit for the looks. Granted, “Lemonade” is not strictly hip-hop—Beyoncé transcends genre at this point—but its sound and attitude certainly has roots in hip-hop's culture, which at the moment might as well be pop culture. (“Hip-pop culture,” Ambrose termed it.)

And that's precisely Ambrose's point. In the early ’90s, hip-hop existed on the margins of pop culture. But as it broke into the mainstream on screen and on the radio throughout the decade, designers embraced the star power wielded by these newly minted icons. Hip-hop is no longer a discrete entity. Now, 2 Chainz flaunts his devotion to Louis Vuitton in “Birthday Song” while Kim and Kanye are staunch #BalmainArmy supporters.

The evolution is not complete. “A lot of the fashion houses still to this day have racist undertones. ... If you're not big and crossover in pop, they don't forecast you in your clothes,” Ambrose said. “But a lot of doors have been broken down.”