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.