10 Moments That Changed Hip-Hop Fashion
Run-DMC rock Adidas, Lil’ Kim steals the show at the ’99 VMAs, Puffy takes Paris and other unforgettable episodes in the history of hip-hop style, detailed by the author of the forthcoming book Fashion Killa.
by Sowmya Krishnamurthy
Fashion has been integral to hip-hop since the art form’s inception. On Aug. 11, 1973, DJ Kool Herc famously threw a party in the rec room of his Bronx apartment building and changed history. The reason for the occasion? His sister, Cindy Campbell, wanted to raise funds for a better back-to-school wardrobe. “I was saving my money, because what you want to do for back to school is go down to Delancey Street instead of going to Fordham Road, because you can get the newest things that a lot of people don’t have,” she told Jeff Chang for his definitive book Can’t Stop Won’t Stop. “And when you go back to school, you want to go with things that nobody has so you could look nice and fresh.” As hip-hop grew from that party into a global force, rappers evolved in fashion as consumers, muses and designers.
It is this extraordinary history that I spent years researching for my new book, Fashion Killa: How Hip-Hop Revolutionized High Fashion, out Oct. 10. Drawing from this unprecedented study, and in celebration of hip-hop’s 50th anniversary, I chose 10 unforgettable moments featuring hip-hop fashion’s trendsetters, iconoclasts and unsung heroes.
Run-DMC: “My Adidas”
Run-DMC propagated the Queens hustler aesthetic — tracksuit, fedora and Cazal sunglasses — and put their favorite sneakers on wax with “My Adidas.” Fans rushed to buy Adidas Superstars, known as shell toes, and wore them without laces, just like their favorite rap group. On July 19, 1986, Run-DMC took the stage at Madison Square Garden and instructed the crowd to hold up their kicks during the song. “Run went out there during the show, ‘D, take it off your feet; hold it up. What’s those? Everybody in here, if you got Adidas on, hold ’em up,’” DMC recalled to Sole Collector. The group’s influence shocked Adidas executive Angelo Anastasio, who was in the house. “So, 40,000 people in a sold-out Madison Square Garden held a sneaker up and Anastasio was like, ‘Oh, my God, it’s true.’” This watershed moment, and a personal video message to Adidas, eventually led to Run-DMC securing an unprecedented endorsement deal for $1 million.
Eric B. & Rakim: Paid in Full
In 1987, Eric B. and Rakim released their seminal debut, Paid in Full. The album was heralded for its precision rhymes, like “I came in the door, I said it before / I never let the mic magnetize me no more.” Just as groundbreaking was the album’s artwork, which featured the duo wearing custom Dapper Dan Gucci jackets. At the time, Dap’s high-end custom looks, or “knock-ups,” were bespoke silhouettes designed in Harlem with luxury logos — Gucci, Louis Vuitton, Fendi — and too expensive for most rappers. “My clothes were expensive, and in the early days of hip-hop, rappers didn’t have money like the hustlers and athletes,” Dap explained in his memoir, Made in Harlem. “In the early days, the rappers were like all of us in the neighborhood, looking up to hustlers on the corner. They wanted to dress like the hustlers.” Working with Eric B. and Rakim for Paid in Full, as well as with LL Cool J, marked the arrival of Dap’s high-end hustler style in hip-hop’s larger zeitgeist, and artists like Big Daddy Kane followed suit. “These were Gucci jackets that look like no Gucci jackets you’ve ever seen,” the author and critic Kelefa Sanneh explained on Soundcheck. “And, in fact, they look like no Gucci jackets that anyone at Gucci had ever seen.”
Snoop Dogg’s Saturday Night Live Debut
“Yo, Andy. It’s Snoop. I want to come check you out.” As the businessman remembered in Fashion Killa, when Andy Hilfiger got a call from Snoop Dogg, who was looking for some free gear, Andy’s brother Tommy had no idea what would happen next. The classic American brand had been shouted out on Grand Puba’s “360° (What Goes Around)” in 1992 (“Girbauds hangin’ baggy / Hilfiger on the top”), but it wasn’t until Snoop wore an unreleased rugby on Saturday Night Live on March 19, 1994 that the red, white and blue exploded in hip-hop.
“Having Snoop Dogg wearing my clothes on TV was such a defining moment — it was the culmination of so many years of hard work,” Tommy told me for Fashion Killa. “I’ll never forget his SNL appearance — overnight, we became a household name.”
“Other designers didn’t get it. They didn’t get into hip-hop,” Andy said. “But Tommy and I? We knew. Wow, this is music and fashion at its finest.” Tommy Hilfiger and hip-hop forged a long bond that included ambassadors like Aaliyah and Treach of Naughty by Nature.
Tupac Shakur, Supermodel
Tupac Shakur symbolized gangsta style with his “Thug Life” tattoo and bad-boy image. He was a champion of early hip-hop designers Karl Kani and April Walker (including appearing in a Karl Kani ad for free). High fashion was drawn to Pac’s rebellious spirit and handsome visage. In 1996, Versace founder Gianni Versace personally asked the rapper to walk in his Fall/Winter menswear runway show in Milan. Gianni and Tupac were kindred spirits as men who lived life to the fullest before dying tragically. There’s some fashion lore that Gianni even called Tupac “the most beautiful man in the world.”
Puffy Takes Paris
Sean “Puffy” Combs made his debut in Vogue in October 1999. The editorial “Puffy Takes Paris,” shot by famed photographer Annie Leibovitz, followed the music impresario and supermodel Kate Moss traipsing through the City of Light and posing romantically on the Pont Alexandre III bridge over the Seine River. Puffy had already established himself as a fashionista in hip-hop. The scion of Andre Harrell had “ghetto fabulous” flowing through his veins and was integral to the aesthetic of artists like Mary J. Blige, Jodeci and the Notorious B.I.G. “The energy felt like Guess Who’s Coming to Dinner with Sidney Poitier,” Puffy reflected years later to Vogue. “That was crazy and before its time.” The Vogue cosign bolstered Puffy’s confidence in being a disruptor in high fashion, and his eponymous Sean John would become one of the most commercially successful and critically acclaimed hip-hop lines of all time.
Lil’ Kim Pops Out at the VMAs
Lil’ Kim is an unsung fashion icon in hip-hop. The diminutive rapper has a career full of memorable looks, from her Hard Core leopard-print-bikini-and-fur combo to a rainbow of wigs in the “Crush on You” music video. But one look stands above the rest. At the 1999 VMAs, Lil’ Kim wore a lavender sequined jumpsuit with her left breast covered by a strategically placed pastie. The custom creation by stylist Misa Hylton, who had previously worked with Mary J. Blige and the Notorious B.I.G., was made with Indian bridal fabric and accented with sparkles and shimmery appliqués resembling a peacock. Even Diana Ross couldn’t help but grab Lil’ Kim playfully onstage. Somehow, the outfit defied a wardrobe malfunction.
JAY-Z Gets Iced Out by Iceberg
There was a time when Iceberg was the hottest brand in hip-hop. The Italian house, known for leather, denim and knits, was considered the paragon of luxury — and the perfect fit for JAY-Z. He was an organic fan of Iceberg and namechecked the brand on songs like 1998’s “Reservoir Dogs” (“Multiple cars and divas with D-Classes / Iceberg sweats with I.B. on the elastic”). However, when JAY-Z and Roc-A-Fella Records co-founder Dame Dash tried to forge a relationship with Iceberg, they were iced out — and told that they could buy some clothes at the sample sale. “They were really, really rude,” Dash says in Fashion Killa. “So at that point I was just like, I’m putting them outta business.” They would use the same independent entrepreneurial ethos that had served them in hip-hop to start their own clothing line. With that, Rocawear was founded in 1999.
Cam’ron Stays Fly in Pink
Everybody wants to see their name in the papers. Back in 2003, Cam’ron wanted to be spotlighted by Page Six, the popular celebrity and gossip hub of the New York Post. In Fashion Killa, he explains that he wore an outrageous pink fur and hat to the Baby Phat fashion show to get the Post’s attention. His flamboyant custom look cost $5,000, and got Cam featured in Page Six. “When I did pink, I did it so I wouldn’t be dressing like everybody else,” he told the New York Times. The ballsy look became his signature, inspiring T-shirts, memorabilia and even MTA subway cards decades later.
Kanye Takes Over Paris Fashion Week
Kanye West began as a preppy schoolboy with a penchant for Ralph Lauren and Louis Vuitton backpacks, but his sartorial persona catalyzed on Jan. 23, 2009, when the rapper-producer and his entourage arrived at Paris Fashion Week. They were attending the Comme des Garçons show, but they were the main event. Kanye wore a blue-and-green peacoat over a buttoned-up blazer, accented by a rose boutonnière, with Louis Vuitton sneakers and a Goyard briefcase. A then-unknown designer named Virgil Abloh wore a bright blue Moncler puffer vest, a Jil Sander marble-print shirt by Raf Simons and red-rimmed eyeglasses. Derek “Fonzworth Bentley” Watkins donned a tan fedora, tilted to one side, with a matching attaché. Don C looked like a drum major in a dark blazer with red trim and gold sneakers, and carrying a Louis Vuitton briefcase. Chris Julian wore a red trench coat and layered plaid, while designer Taz Arnold put on snug leopard-print leggings, a fitted green leather jacket and a wild cowboy hat. “I saw Kanye and his posse walk from their car towards us and there was no paparazzi. They saw me and the one other photographer there, and just stopped to assemble in formation in front of us,” said photographer Tommy Ton, who captured the posse, to Vogue. The iconic moment marked Kanye’s arrival as a sartorialist; he was serious about being taken seriously.
Young Thug in a Dress
“In my world, of course, it don’t matter, you know — you could be a gangsta with a dress,” Young Thug said in a 2016 Calvin Klein ad. “Or you could be a gangsta with baggy pants. I feel like there’s no such thing as gender.” The Atlanta rapper refused any boundaries, in fashion or in music, and proved that with the cover of his Jeffery mixtape the same year. Thug wore a dress by Alessandro Trincone that featured soft baby-blue ruffles in a silhouette inspired by a Japanese samurai warrior, with a reimagined kosode cloak and jingasa hat. “It’s like Mortal Kombat … Sub-Zero,” the rapper told V Files. It took hours to put the dress on and style it just right. Even the designer was shocked how good the rapper looked in the delicate garment. “I was literally shocked because Young Thug and me — I don’t know,” Trincone said to Complex. “But I said, ‘OK, let’s try it.’ Then when I saw the cover, I was like, ‘Oh, my God. I did it.’ I liked it.” With that, Thug solidified himself as a fashion rebel, fearless enough to wear anything he wanted.
