Every era has its own style godheads. The party-hardy kids of the early aughts raided thrift stores for Mick’s and Keith’s slinky silk shirts and the Ramones’ badass biker jackets. Some 10 years later, Paul Newman, Steve McQueen, and Muhammad Ali populated the Tumblr mood boards of guys negotiating the relationship between masculinity and their newfound obsession with clothing. Now, as we hurtle headfirst out of a global pandemic and into what some predict to be a new Roaring Twenties, there’s no one particular decade, tribe, or figure that serves as a style North Star. Which is precisely why it’s never been more exciting to get dressed—the guardrails have fallen, and men’s fashion is now the ultimate choose-your-own-adventure game.
Out of this wonderful chaos, a new constellation of style inspiration has emerged. Some of the names on this list are ones you might expect (hello, Kurt), while others have not yet been elected to the style hall of fame (ciao, Pavarotti). But all are musicians who fashioned an image for themselves and then completely and fearlessly embodied their look. As we go outside, to work, to parties, to weddings, nothing feels more important than embracing radical self-expression. These men are all avatars of sincere dressing—unflinching personal style—which is probably why their spirits were very much present on the spring-summer 2021 runways. Let their looks be your guide in these uncertain, optimistic times.
Kurt Cobain | 1990
Ten minutes before going on for a show at Hampshire College, Kurt asked Nirvana’s publicist if he could borrow her dress. “There’s nothing more comfortable,” the grunge king turned fluid-fashion icon would later say, “than a cozy flower pattern.”
Gucci | Spring 2021
No designer has channeled the promise of Kurt’s radically attitudinal, madcap style quite like Gucci’s Alessandro Michele, who grew up idolizing Nirvana. Now he’s at the forefront of fashion’s gender-fluid movement, creating dresses fit for rock stars. (Harry Styles even wore one on the cover of Vogue.)
Tupac | 1994
Tupac’s relentlessly authentic style laid the groundwork for the nascent streetwear industry, and he helped kick off fashion’s obsession with hip-hop culture when he walked in a Versace show in 1995. He remains a steadfast reference point for contemporary designers: His fits—for instance, mixing the swagger of workaday denim with the power of a leather vest—are as relevant as ever.
Raf Simons | Spring 2021
This season Raf Simons celebrated a quarter century in fashion, a tenure animated by the intoxicating touchstones of youth style. The fitted leather vest he created has a style legacy that stretches from outlaw biker gangs to the ’80s post-punk scenes of Simons’s teenage years.
Angelo Moore | 1993
With his perpetually unbuttoned graphic shirts and fiery shorts—a practical uniform for his intensely aerobic stage-diving performances—the frontman of ska-punk band Fishbone became an alt-style icon for a generation of politically minded West Coast rebels.
Celine Homme | Spring 2021
Hedi Slimane introduced a revolutionary Strokes-y silhouette to men’s fashion in the early aughts; now he designs his collections around sexy music subcultures. This season he looked to the fearless dressers, dancers, and musicians of TikTok, whose freaky style syncs perfectly with that of cult-music legends of the past.
Jarvis Cocker | 1995
Pulp slept in tents after accepting a Glastonbury headline slot at the last minute, but the frontman of the legendary Brit-pop band, Jarvis Cocker, still pulled up in a velvet double-breasted pinstripe suit and coordinating awning-striped shirt and tie. “I couldn’t live like that, to be honest,” he said of the hippie-dippie Glasto lifestyle.
Ralph Lauren | Spring 2021
The secret to Ralph Lauren’s success is that the prep god has always been a rule breaker. You might not want to wear this razor-sharp suit to a mud-pit music festival, but nothing should stop you from defying convention and pairing it with a Cocker-esque candy-striped shirt and tonal tie.
Miles Davis | 1987
In the ’80s, Miles Davis’s style shifted thanks to Prince’s paradigm-disrupting influence: Out were the Sunday-best suits and in were the piles of gold jewelry, slinky silk shirts, and canary yellow jackets. (The Prince of Darkness bought a yellow Ferrari to match.)
Louis Vuitton Men’s | Spring 2021
Designer Virgil Abloh is a master of multilayered references, his Louis Vuitton shows brimming with nods to great Black sartorialists of yore. This season Abloh paid tribute to his pops, a Ghanaian immigrant who proudly dressed in the jazzy tradition of cats like Miles.
Tom Petty | 1977
With his matchstick trousers, silk cravat, and epically heeled snakeskin boots (procured, according to a fellow Heartbreaker, in London), Tom Petty took the rail-thin-rocker aesthetic of Dylan and updated it for the post-Summer of Love generation.
Prada | Spring 2021
You can find the spirit of Petty alive and well in the back of vintage rock-and-roll stores, or you can go to Prada, where his sleek drip has been reimagined for 2021 in a suit made from ultra-comfortable techno-stretch fabric.
Fela Kuti | 1986 (left), 1975 (right)
For the Black President, who did rock star style his own way, wearing traditional Ankara jumpsuits (and occasionally nothing more than his underwear) was as revolutionary a statement as his sublime Afrobeat sound.
Bottega Veneta | Spring 2021
At Bottega Veneta, achingly luxurious materials speak louder than logos, and this season designer Daniel Lee married the power of the jumpsuit (a uniform for generations of iconoclastic artists) with the gorgeous tactility of a lightweight striped bouclé fabric.
Orlebar Brown | Spring 2021
There’s nothing to wearing a retro-striped swim brief this summer—all you need is approximately one-hundredth the confidence of Fela, and maybe some loafers, to go with it.
Luciano Pavarotti | 1991
The larger-than-life tenor was best known for flourishing a white handkerchief onstage, but he also had an extensive collection of flamboyant Hawaiian shirts, which became his off-duty uniform when cruising around his villa on the Adriatic Sea.
Paul Smith | Spring 2021
With its gothic rose print, Sir Paul Smith’s floral shirt speaks to the current moment but retains the best part of the ’90s Hawaiian essential: that loose-and-flowy Pavarotti fit.
Willie Nelson | 1978
Ever since the ’70s, when he grew his hair out and joined the Outlaw Country movement, Shotgun Willie has been the patron saint of louche stoners everywhere. The most important commandment? Thy shall not wear sleeves.
Amiri | Spring 2021
Mike Amiri looks at the world through wonderfully-sleazy yellow-tinted glasses, and his collections channel the influence of the psychedelic travelers and blazed-out rock stars who once prowled the clubs of L.A.
A version of this story originally appeared in the April 2021 issue with the title “Bite This Style.”
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Still life photographs by Martin Brown
Styled by Jon Tietz
Collages by Simon Abranowicz
Prop styling by Liz Serwin for Judy Casey Inc.