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Over the years, the Met Gala has evolved from a traditional evening gala with a strict dress code to a high-fashion event where celebrities are encouraged to take risks and push boundaries. Early on, men typically opted for classic suiting or tuxedos, but there were a few notable exceptions. In 2001, Alan Cumming wore a red tartan kilt, and in 2006, Alexander McQueen sported a tartan print in a nod to his Scottish heritage. Marc Jacobs made headlines in 2012 when he wore a lace dress over boxer shorts, eschewing the typical tuxedo for a more daring look.

In the 2010s, male stars at the Met Gala began to embrace a more adventurous and free-spirited approach to fashion. Designers like Jacobs declared that being “boring” was no longer acceptable, leading to a surge of bold and unconventional looks on the red carpet. Jaden Smith made a statement in 2017 by carrying his own dreadlocks, while Chadwick Boseman and Jared Leto both fully embraced the gala’s theme with their outfits in 2018 and 2019, respectively. These out-of-the-box ensembles became some of the most memorable moments from the past decade.

At the 2021 Met Gala, men in Hollywood raised the bar for theatrical red carpet style with striking ensembles that showcased their individuality and creativity. Lil Nas X made a bold statement by wearing three different Versace creations, while A$AP Rocky opted for a quilted cape that perfectly complemented Rihanna’s outfit. In 2022, stars like Jared Leto, Gunna, and Alton Mason brought their best Gilded Age suiting to the event, continuing the trend of pushing boundaries and embracing unique styles.

Last year’s gala, which honored Karl Lagerfeld, featured dramatic and memorable menswear looks that paid tribute to the late designer. Jeremy Pope’s Balmain cape revealed Lagerfeld’s portrait on a long train, while Alton Mason dressed as one of Lagerfeld’s iconic Chanel brides. Bad Bunny’s white Jacquemus look also nodded to bridal style, adding a touch of whimsy and creativity to the red carpet.

As fashion enthusiasts eagerly anticipate the menswear looks at the upcoming 2024 Met Gala, it’s clear that the event continues to be a platform for male celebrities in Hollywood to showcase their individuality, creativity, and willingness to take risks in their sartorial choices. The 50 best dressed men in Met Gala history have set a high bar for red carpet style, pushing boundaries and redefining traditional notions of menswear fashion at one of the most iconic and influential fashion events of the year.

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