Jean-Michel Basquiat, Comme des Garçons men’s 1987
Like his friendship with Andy Warhol, Jean-Michel Basquiat’s relationship with Comme des Garçon was both devoted and contentious. Andy kept meticulous notes about Basquiat’s Comme obsession in his diary. He noted the CDG jacket Basquiat left at a hotel while high, the CDG shopgirl who allegedly used him for money, and the CDG fashion show at which said shopgirl dumped him. (“She said he looked like a fool out there on the runway modeling the clothes and that’s when she finally was over him,” Warhol wrote.) Well, we think SAMO looked pretty sharp in two different double-breasted grey suits, complete with a bowtie and patent leather Mary Janes.
Madonna, Jean Paul Gaultier 1992
After creating the iconic conical corset for Madonna’s Blond Ambition Tour in 1990, Jean Paul Gaultier became fashion royalty. For his first-ever runway show in 1992, he staged a star-studded extravaganza to raise awareness of AIDS, featuring models and sex-positive celebrities like Billy Idol and Dr. Ruth rocking rubber, leather, toilet paper, and assless chaps. In a seemingly demure finale, the designer walked with his main muse, Madonna, on his arm. She wore an oversized blazer, a chic beret, and a single gold tooth. As the pair neared the end of the runway, however, her Madgesty slowly removed her coat and exposed her breasts in an unscripted act of rebellion. “I was supposed to wear a top and jacket like Jean Paul’s, but at the last minute I decided it was better to go out topless!” she said.
Tupac Shakur, Versace men’s 1996
Before
Migos
had even uttered their first words, Versace was embracing hip-hop in a way no fashion house had before. Gianni Versace reportedly found Tupac
to be
“the most beautiful man in the world” and showered his friend with the kind of brightly patterned silk tops that would now be essential in a “90s rapper” starter pack meme. Pac called this out in his infamous Biggie and Puff diss track “Hit ‘Em Up,” with his lyric “Now it’s all about Versace, you copied my style.” He also showed everyone who truly reigned supreme in Versace when he walked the runway for the brand’s 1996 menswear show — in a gold suit and chains, with fiancé Kidada Jones on his arm and two bodyguards trailing close behind.
Chloë Sevigny, Miu Miu spring/summer 96
In 1993, Miuccia Prada launched Miu Miu, a modern and rebellious sister line for Prada and fittingly snatched up “the coolest girl in the world” for the brand’s first campaign in 1996. For the spring/summer show of that year, a then-teenage Chloë Sevigny walked alongside Kate Moss in a lavender leather midi skirt and matching mules, paired with a black boatneck sweater. Since then, Chloë has appeared in countless campaigns (including a return to Miu Miu 16 years later), #frows, and fashion collabs, but remained absent from the runway until Carol Lim and Humberto Leon’s first collection for Kenzo in spring/summer 12.
Patti Smith, Ann Demeulemeester men’s fall/winter 06
Kindred spirits Patti Smith and Ann Demeulemeester crossed paths years before they actually met. As a student, the now legendary Belgian designer was awestruck by the casual cool of Smith’s 1975 album cover for Horses. And she chose Smith’s “Waves” as the soundtrack for her first Paris show, in 1991, sending the musician a white T-shirt as a thank you. After more than five years of corresponding, the duo officially collaborated on Demeulemeester’s spring/summer 00 collection, “Woolgathering.” Demeulemeester hand-embroidered Smith’s powerful lyrics onto delicate layers of tulle and silk, while models walked the runway and Patti read aloud from her book of short stories Woolgathering. In 2006, Patti finally walked Demeulemeester’s runway herself, during the designer’s spring/summer 06 menswear show. She carried a clarinet, and exuded the same disheveled, androgynous cool that caught Demeulemeester’s eye 30 years before.
Related: The seven best music-meets-fashion crossovers
Grace Jones, Diesel fall/winter 06
Issey Miyake recognized Grace Jones’ star power the instant he met her in Paris, in 1976. Captivated by her unusual beauty and irrepressible charisma, he arranged to tour 12 top black models from around the world in a kabuki-theater style performance wearing his pleated designs. Jones remembers the show in her 2015 memoir: “Who else would think of using only black girls, even now? This was girl power from Mars.” The tour was a global sensation, and Jones’ fashion star was in the ascendant. She walked Kenzo’s infamous Studio 54 fashion show in 1977 and Alaïa fall/winter 85. Then, after a nearly 30-year fashion week hiatus, Jones returned to the runway for Diesel’s fall/winter 06 collection. Clad in studded bondage leather, and thigh-high boots, she stormed the runway at the age of 56.
Rihanna, DSquared2 spring/summer 08
Less than a decade before presenting her own collection during NYFW, Rihanna had her first taste of fashion week on the DSquared2 spring/summer 08 catwalk. Soundtracked by her hit song “Shut Up and Drive,” the bad gal emerged from a hot rod, threw her keys to the chauffeur, and strutted her stuff in a black babydoll slip, before striking a classic hand-on-hip pose. If you think Rih makes her first go at the runway look too easy, remember this is the woman who can float across sidewalk grates in stilettos.
Related: Backstage at Rihanna’s first Fenty x Puma show
Pamela Anderson, Vivienne Westwood fall/winter 09
Outspoken eco-warrior Vivienne Westwood invited equally staunch animal rights advocate Pamela Anderson to close out her fall/winter 09 show, but that night the two activists ended up campaigning for a totally different cause: #FreeTheNipple. The Dame and Baywatch bombshell had met earlier that year, at Westwood’s Red Label show, and become fast friends, so nobody was too surprised when they closed out the show arm-in-arm. However, there were more than a few gasps in the crowd when Pam’s nipple accidentally slipped out of her black punk-geisha gown.
Lady Gaga, Mugler fall/winter 11 and Marc Jacobs fall/winter 16
After her sophomore album Born This Way, Lady Gaga became as known for decadent style as for her infectious dance pop hits. Naturally, Mother Monster’s then-stylist and BFF Nicola Formichetti — the mad genius behind outlandish looks like her raw meat dress — tapped Gaga for his debut collection as Mugler’s creative director. In waist-length pigtails, she energetically clawed the air, body rolled, and puffed a cigarette as she made her way down the catwalk to the premiere of her song “Government Hooker.” Last season, she made a more subdued return to the runway, processing with Marc Jacobs’ gothic lolitas (though she still wore eight-inch platforms).
A$AP Rocky, Hood By Air fall/winter 13
For cult brand Hood By Air’s inaugural runway show in New York, then-rookie designer Shayne Oliver nabbed buzzy Harlem rapper A$AP Rocky to rep his final look, propelling both of their careers into the big leagues. Wearing a backwards white cap, neoprene jacket, and drop-crotch pants, Rocky became the face of hypebeasts everywhere — for about a year. The rapper later dissed the brand on track “Multiply,” by sort of explaining, “I birthed it, so I can kill it.” Last year he went on record to state that “celebrities ruined fashion,” but that didn’t stop him from starring in Dior Homme’s latest campaign nor collaborating with J.W. Anderson on a capsule collection.
Beth Ditto, Marc Jacobs spring/summer 16
For one night only, Marc Jacobs brought the stars of New York’s iconic Ziegfeld Theatre back from the dead for his extravagant spring/summer 16 collection. He also gave the fashion world life the moment he sent Gossip singer, outspoken feminist, and close friend Beth Ditto down the red carpet. Wearing a sequined ivory silk gown, she exuded 1940s-Hollywood glamour and stole the show. Since her epic runway moment, Beth has gone on to appear in MJ’s star-studded campaign, launch an eponymous collection, and release a line of plus-size corsets with Jean Paul Gaultier — for whom she made her runway debut in 2011 with a literal mic drop performance.
Dev Hynes, Eckhaus Latta spring/summer 16
Experimental design duo Mike Eckhaus and Zoe Latta sent a slew of “nodels” (non-models) down their spring runway last year. A cast of downtown New York’s coolest, including Grace Dunham, Michael Bailey-Gates, took over a converted furniture showroom. The star of the show, though, was Devonté Hynes — wearing easy, overdyed chambray and a brimless leather baseball cap — who proved he could still stand out without making a sound. At the brand’s previous show, Hynes had performed live while models walked, and he recently provided the score for the brand’s surreal collaborative film “Roach.”
Credits
Text Taylor Ford