The Met Gala’s red carpet is a place where celebrities are encouraged to pull out all the stops. So long as they honor the year’s specific theme, all fashion rules pretty much go out the window. But this wasn’t always the case. In earlier years, the event was more of a traditional evening gala, where men adhered to an especially conventional dress code, mostly opting for classic suiting or tuxedos.

Though few and far between, there were some risk-takers in the early Met Gala days. Back in 2001, Alan Cumming ascended the stairs of the museum in a red tartan kilt (the theme that year was “Jacqueline Kennedy: The White House Years,” showing no real connection to his bold ensemble). Later in 2006, the late designer Alexander McQueen also hit the red carpet in a tartan print that he matched to his date for the evening, Sarah Jessica Parker, seemingly as a nod to his Scottish roots. And who could forget that time Marc Jacobs wore a lace dress by Comme des Garçons over boxer shorts back in 2012? “I just didn’t wanna wear a tuxedo and be boring,” the designer later said of the look.

In the 2010s, after a surge of experimentation at men’s fashion shows, male stars at the Met began to adopt a more free-wheeling spirit. As Jacobs said, “boring” was no longer acceptable. Out went the suits, in came the outré looks. Some of the best moments in the past decade have been entirely out of box. Jaden Smith offered up the wildest example of this when he carried his own dreadlocks on the carpet in 2017. Other winning ensembles have come as the result of absolute commitment to a theme. Take Kanye West’s robotic Balmain look from the technology theme in 2016; Chadwick Boseman’s angelic Versace cape for the “Heavenly Bodies” theme in 2018; Jared Leto, who went full-on camp in 2019, with a prosthetic of his own head designed by Gucci’s Alessandro Michele tucked under his arm.

With the 2020 Met Gala postponed last year, men in Hollywood have been afforded extra time to mull over their red carpet looks. But the 2021 Met Gala is rapidly approaching on September 13th, and, chances are, the best of them will push the envelope even further forward.

Below, the 24 best-dressed men in Met Gala history.

Jared Leto in Gucci2019

Harry Styles in Gucci2019

Billy Porter in The Blonds2019

Sean “Diddy” Combs and Christian Combs2018

Takeoff, Quavo, and Offset (of Migos) in Versace2018

Chadwick Boseman in Versace2018

Zayn Malik in Versace (with Gigi Hadid)2016

Neil Patrick Harris and David Burtka in Thom Browne2014

Alexander McQueen (with Sarah Jessica Parker)2006

Zac Posen (with Raquel Zimmermann)2005