Every year, 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 Chadwick Boseman’s angelic Versace cape for the “Heavenly Bodies” theme in 2018; or 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.

At the 2021 American fashion-themed Met Gala, men in Hollywood took theatrical red carpet style to staggering new heights. Rapper Lil Nas X wore three bold Versace creations on the carpet—including an ornate cape, gold armor, and glitzy bodysuit. A$AP Rocky also wore a quilted ERL cape, which perfectly complemented Rihanna’s voluminous Balenciaga design. At the 2022 Met Gala, stars like Jared Leto, Gunna, and Alton Mason brought forward their best Gilded Age suiting.

More recently, at the 2023 gala honoring Karl Lagerfeld, Jeremy Pope chose a dramatic Balmain cape, which extended to reveal a long train bearing the late designer’s portrait. Alton Mason, also dressed in Balmain, showed up as one of Lagerfeld’s iconic Chanel brides. Last year, meanwhile, Morgan Spector and Colman Domingo stood out in sharp-shouldered Willy Chavarria suiting. Bad Bunny went more avant-garde in his deconstructed Maison Margiela suit—complete with a theatrical chapeau, of course.

As we await the menswear looks on the 2025 Met Gala red carpet, below, see the 57 best dressed men in Met Gala history.