Dressed Like Rappers
Once upon a time, high-fashion brands shunned hip-hop. Yet today, these same luxury designers are drapping and dripping rappers in their exorbitant threads. How did the dress code switch happen?
Words: Sowmya Krishnamurthy
Editor’s Note: This story originally appeared in the Winter 2018 issue of XXL Magazine, on stands now.

Diddy is shirtless, lounging in leather pants with a crucifix chain dangling over his taut, tatted-up torso. The rapper languidly watches Scarface, oblivious as supermodel Kate Moss is draped in a see-through gown with a cigarette nearby. A fantasy of aspiration, elan and wealth, it’s the stuff rap dreams are made of. In 1999, renowned photographer Annie Leibovitz shot this and other images for Vogue’s October spread, “Puffy Takes Paris.” The Bad Boy mogul basked among bold names like Jean Paul Gaultier, Karl Lagerfeld, Oscar de la Renta, Alek Wek and John Galliano. It’s a landmark moment with hip-hop front and center in high fashion’s bible.

The relationship between hip-hop and luxury fashion has always been tenuous, a gradual process of acceptance. “Hip-hop embraced fashion before fashion embraced hip-hop,” says Kyle Luu, a stylist and creative director who has worked with artists like Travis Scott and Young Thug. “Fashion people are always late to the party.” Yet in the past year, hip-hop and fashion have been inextricably intertwined more than ever. Cardi B scored a seat next to Vogue’s powerful editor-in-chief Anna Wintour during Alexander Wang’s show at New York Fashion Week. You can’t flip a glossy magazine without seeing A$AP Rocky’s visage in underwear ads for Calvin Klein. Versace has a sunglass line—inspired by the shades made iconic by The Notorious B.I.G.—sold at Barneys.

Louis Vuitton, Marc Jacobs, Yves Saint Laurent and a slew of others have featured rappers like Playboi Carti, Princess Nokia and Travis Scott, respectively, in their promotions. A$AP Ferg, Migos, Nicki Minaj and Childish Gambino were among the glitterati at the ultra-exclusive 2018 Met Gala, which featured a promo video of Wintour set to Coolio’s “Gangsta’s Paradise.” “It’s like, a party that everybody wants to be invited to,” says Ferg about the cozy pairing. Hip-hop and high fashion aren’t just at the same party; they’re the best of friends.

Frazer Harrison/Getty Images

It wasn’t always feel-good vibes. Hip-hop has embraced looking fresh since its inception—Run-DMC’s unlaced Adidas to LL Cool J’s Kangol hat and ubiquitous rope chains worn by artists like Slick Rick—but luxury brands were wary to work with what was seen as a fringe genre or even a passing fad. Because of this, rappers in the early days had to get plucky. Harlem tailor extraordinaire Dapper Dan famously created counterfeits of Gucci, Fendi, Louis Vuitton and MCM to serve his clients like Big Daddy Kane, Rakim and Salt-N-Pepa. Misa Hylton, fashion architect and founder of Misa Hylton Fashion Academy, remembers the challenges of getting past gatekeepers at brands and publicity firms to gain access to clothes—referred to as “pulling”—for clients like Mary J. Blige and Jodeci. “For me, pulling clothes was almost nonexistent in the beginning,” she says. “There weren’t many doors that were open. Luxury designers weren’t willing to create relationships with me.” Hylton, like Dan, leveraged her talents to create custom looks to bypass the bottleneck in the system. “I decided to design and create garments that I wanted, and that I knew my clients would love.”

There isn’t one definitive reason why luxury brands weren’t fucking with hip-hop. Many were—and still are—notoriously guarded over which celebrities get to wear and subsequently publicize their clothes. Having the right garment on a problematic celebrity can spell backlash. The fact that the majority of luxury brands are old, European houses has likely fueled ignorance (and even flat-out racism) against rappers and the communities of color that they reflect. “Early on we had many strikes against us, as far as being African-American, young and unknown,” says Hylton, who went on to work with artists like Lil’ Kim, Missy Elliott and Diddy. “Luxury stores in the past didn’t treat people of color with the dignity I think they deserve,” Dan told The New York Times in March 2018, two months after opening an appointment-only boutique with Gucci. Back in the late 1980s, he faced lawsuits on allegations of copyright violation and was raided on behalf of Fendi. Sums up Luu, “I mean, let’s call a spade a spade: It’s a bunch of rich, White people who work in fashion.”

As hip-hop gained momentum—both financially and as the cultural force of cool—the pendulum began to sway. Fashion brands realized hip-hop was beneficial to the bottom line. “When something is hot and makes money, people want to now figure out how to do business and get down with it,” says Hylton. The “rich, White people” took notice and worlds began to bleed into one another. By the late 1990s, hip-hop was packaged as “ghetto fabulous” and “bling” was on the tip of everyone’s tongues. The wave continued. In 2003, Jay-Z and Pharrell—who would later make the humongous Vivienne Westwood buffalo hat his staple—were bopping with Naomi Campbell and supermodels in the music video for “Change Clothes.” That same year, Diddy won the Menswear Designer of the Year Award for Sean John from the prestigious CFDA (Council of Fashion Designers of America), besting vets Ralph Lauren and Michael Kors. Lil’ Kim became muse (and best friends) with Marc Jacobs while behind bars in 2005. Years after Kanye West first began calling himself the “Louis Vuitton Don” he landed a signature sneaker with the French brand in 2009.

Bertrand Rindoff Petroff/Getty Images

But the doors didn’t open for everyone simultaneously. The same year that Kanye’s LV kicks hit retail, Rick Ross was caught up in a controversy surrounding a pair of Louis Vuitton shades that he sported on the cover of XXL’s May 2009 issue. A legal rep for the fashion house released a statement disassociating the bearded rapper from the brand and insisting that the sunglasses were counterfeit. In actuality, the shades were authentic, according to Jacob Bernstein (a.k.a. The Sunglasses Pimp), who told AllHipHop that he’d customized Ross’ eyewear with solid gold accents.

Still, the overall success of rap figures in the upper echelon of fashion has lowered the barrier to entry for today’s hip-hop crop. But let’s be clear: There’s still a velvet rope. Rappers—especially new artists or those without mainstream recognition—need to prove themselves. “Some [labels] pick and choose if you’re not the It guy or It girl,” says Zoe Dupree, a wardrobe stylist and creative director who has worked extensively with Young Thug. “They want to get their stuff onto people in the media or people constantly doing stuff. It’s no brand in particular. Some people want their stuff on artists that are hot off the presses.” Dupree shares that Thug mostly buys his own clothes but the establishment has taken notice of the reaction the rapper receives for his daring, avant-garde style, such as the pale blue Alessandro Trincone dress that he wore on the cover of Jeffrey. The garment was heralded as a gender-fluid moment by Women’s Wear Daily, Huffington Post and Snobette. “He’s been making impacts with fashion. Every time he places the garment on, he’s making headlines,” says Zoe.

Luu faced similar hurdles with Travis Scott in the beginning. “There were designers who were always on board: Alexander Wang, Alexander McQueen, there were a bunch of people who were supportive from the jump,” he says. “But that’s because they had PR people [who] did their homework and knew what was good.” Once the “Sicko Mode” rapper hit critical mass, haters were converted into fans. “The other people would just say no all the time until it reached a certain level in his career where they offered him to be the face of the campaign. Fashion people are leeches. They just leech on to whatever.”

Peter White/Getty Images

Following the success of A$AP Mob and A$AP Rocky, Ferg had to prove himself as a solo force among the fashion cognoscenti. “I had to get on their radar, of course,” he says. “I had to work my way up to the ranks of even being noticed.” The rapper used to design his own accessories—worn by Swizz Beatz and Chris Brown—and buy off the rack in the early days. His Harlem swag and penchant for popping tags were a natural fit for high fashion. The hook on 2017’s “Plain Jane” is an ode to nice jewelry: “Ben Baller did the chain/Tourneau for the watch/Presiplain Jane.” He’s since been involved in some dozen collaborations, including working with Calvin Klein and Valentino, and performing at Tiffany & Co.’s flagship store. At this stage, working with Ferg is ostensibly more beneficial for the designer than to him and he’s incredibly selective about what he supports. “I have to believe in them,” says Ferg while dressed in Burberry sweats, Pyer Moss and jewelry gifted by Tiffany & Co. “It can’t be like something that just up and appears and disappears tomorrow. It has to be something I can follow and respect the designer as an artist.”

Ferg foresees hip-hop becoming more embedded in high fashion, with rappers pivoting into becoming designers. “We all artists in a way,” he says. “It’s gonna be cool for rappers to make brands. Soon it’s gonna be like, ‘Alright these guys like fly stuff. They design fly stuff. Let’s give them their own brand.’” Dupree sees more people with hip-hop sensibility penetrating leadership, noting how Virgil Abloh—Kanye West’s protégé and designer of Off-White—secured the post as Men’s Artistic Director at Louis Vuitton. “There’s people pushing the envelope,” he explains. “The fashion industry used to be White-dominated. Now, there’s people like Virgil that’s giving a lot of people inspiration to wear the brand, spread awareness and give a different dynamic for high luxury brands.” Hylton agrees that hip-hop is here to stay in high fashion. “Hip-hop is continuously evolving. It’s not just one particular style that is driving the movement. It’s a way of life. It’s a culture.” No matter what incarnation hip-hop is in, it’s the barometer of cool—and that’s something fashion can’t resist. “Hip-hop style always offers something new,” says Hylton. “It continues to cement us in fashion history and at the same time, gives us our seat in the future of fashion. It’s the gift that keeps on giving.”

NurPhoto/Getty Images

Check out more from XXL’s Winter 2018 issue including our Migos cover story interviewVic Mensa's turn toward activism and a woman's equality proponent, Show & Prove with Jay Critch, G Herbo finding new purpose as a father, Show & Prove with Asian Dolla look at the way women in hip-hop are rising to higher heights, Smokepurpp breaking down the songs on Deadstar 2, Show & Prove with YBN Cordae and more.

See Photos of A$AP Ferg's Different Looks Over the Years