The 15 Best Men’s Fashion Moments in Met Gala History

As the first Monday in May nears, take a stroll down memory lane with a look at the best menswear looks over the years.

man with long brown hair and crown waving on red carpet
The first Monday in May is just around the corner. Ray Tamarra/GC Images

As the fashion world buzzes with anticipation ahead of the Costume Institute’s annual Met Gala on May 1, and this year’s tribute to the iconic Karl Lagerfeld through the theme, “A Line of Beauty,” we can’t help but reminisce about the dashing gentlemen who have left their mark on the event’s red carpet. The Met Gala, an exclusive playground for fashion’s elite, challenges its attendees to push the boundaries of style with thought-provoking and captivating themes. Dressing for the Met Gala is an art form that could (and perhaps should) be studied meticulously—play it too safe at this so-called Super Bowl of fashion, and you’ll fade into obscurity.

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So let’s raise our glasses to the all-time best-dressed men at the Met Gala—fashion icons such as Marc Jacobs, Timothée Chalamet, Diddy, and so many more. From avant-garde black tie ensembles to gender-bending creations, these gentlemen have left the world awestruck with their unparalleled stylish flair and fashion bravado. So, grab a cocktail and join us as we saunter down memory lane, celebrating the Met Gala’s most unforgettable menswear moments, all while eagerly awaiting the upcoming extravaganza of the Lagerfeld-inspired 2023 event on the first Monday of May.

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Heavenly Bodies: Fashion & The Catholic Imagination Costume Institute Gala
Chadwick Boseman. FilmMagic

Chadwick Boseman, 2018

Heavenly Bodies: Fashion and the Catholic Imagination

Chadwick Boseman made Met Gala history in a jaw-dropping Givenchy Haute Couture piece. The intricately embroidered white suit was perfectly tailored and featured a dramatic, floor-length cape adorned with crosses. Boseman’s ensemble was nothing short of heavenly.

man in black lace outfit on red carpet At Costume Institute Benefit
Marc Jacobs. Corbis via Getty Images

Marc Jacobs, 2012

Schiaparelli and Prada: Impossible Conversations

Always daring to be different, Marc Jacobs rocked a Comme des Garçons lace polo dress, complete with boxer shorts and pilgrim shoes. This rule-breaking getup paid tribute to the fearless spirit of Schiaparelli and Prada, turning heads and raising eyebrows in equal measure.

man in black skirt and jacket on red carpet
Oscar Isaac. Getty Images for The Met Museum/

Oscar Isaac, 2022

Gilded Glamour

Oscar Isaac and his spouse, Elvira Lind, delivered a tasteful execution of gender-fluid fashion in matching grey structured looks by Thom Browne. Isaac sported a dress while Lind wore a suit, proving that fashion knows no gender boundaries. Isaac’s refined masculinity shone through, making this memorable ensemble a bold statement on the red carpet.

actor adrien brody in sparkling jacket on red carpet
Adrien Brody. WireImage

Adrien Brody, 2015

China: Through the Looking Glass

While many Met Gala attendees interpreted “China” as an invitation for heavy embroidery, Adam Brody struck the perfect balance with a tasteful, lounge-ready look. Sporting a silk double-breasted jacket with a velvet lapel, the actor’s outfit was decadent and nostalgic without going overboard. The subtle embroidery added just the right amount of dapper elegance.

actor jared leto in navy robe and gold accessories and crown on red carpet
Jared Leto. Getty Images

Jared Leto, 2018

Heavenly Bodies: Fashion and the Catholic Imagination 

Jared Leto channeled his inner deity in a striking Gucci creation, complete with a regal, jewel-encrusted crown. The look masterfully blended religious iconography and high fashion, featuring a lavishly embroidered, floor-length cape and impeccably tailored suit, all with that signature Gucci flair.

man in black and white outfit on red carpet
Sean ‘Diddy’ Combs. WireImage

Diddy, 2017

Rei Kawakubo/Comme des Garçons: Art of the In-Between

Leave it to Diddy to pull off an avant-garde black tie look with plenty of panache. This daring combination, designed by Rick Owens, featured a tailored blazer with an asymmetric hem, which he paired with tailored trousers and black leather boots. The pièce de résistance? A dramatic floor-length cape that commanded attention with every step.

actor joshua jackson in black suit on red carpet
Joshua Jackson. Bryan Bedder/WireImage for Vogue

Joshua Jackson, 2010

American Woman: Fashioning a National Identity

Channeling old-world charm, Joshua Jackson donned a dashing three-piece suit by Tom Ford. The rich, deep blue hue and bold bow tie perfectly embodied the spirit of American fashion history.

man in white tie jacket with woman in black sparkly dress on red carpet
Gary Oldman and Alexandra Edenborough. Dimitrios Kambouris/Getty Images

Gary Oldman, 2012

Schiaparelli And Prada: Impossible Conversations

Gary Oldman, ever the style chameleon, opted for a classic tuxedo by Prada with a twist. The sartorial moment was accentuated by a bold, polka-dotted tie, adding an unexpected pop of color and pattern to an otherwise traditional look.

man and woman in matching red plaid kilt tartan outfits on red carpet
Alexander McQueen and Sarah Jessica Parker. Evan Agostini/Getty Images

Alexander McQueen, 2006

AngloMania: Tradition and Transgression in British Fashion

Alexander McQueen, a master of transgressive fashion, donned an ensemble that seemed to be a gesture to his Scottish heritage, with Clan Macqueen tartan at the 2006 Met Gala. The kilt, paired with a fitted black blazer and knee-high socks, showcased McQueen’s ability to honor tradition while still pushing boundaries.

Andre Leon Talley with Renee Zellweger at 2004 Costume Institute Gala 'Dangerous Liaisons'
Andre Leon Talley with Renee Zellweger. Ron Galella Collection via Getty

Andre Leon Talley, 2004

Dangerous Liaisons: Fashion and Furniture in the 18th Century

Fashion legend Andre Leon Talley made a grand, unapologetically dramatic entrance at the 2004 Met Gala in a floor-length, cape-style trench coat by Yves Saint Laurent. The billowing, larger-than-life silhouette, complete with over-exaggerated sleeves, oozed an air of intellectual swagger.

man in navy jacket and bow tie
Nicholas Hoult. Getty Images

Nicholas Hoult, 2013

Punk: Chaos to Couture

Nicholas Hoult injected a dose of punk into high fashion with a daring, unconventional outfit by Tom Ford. Sporting a studded jacket, slim trousers, and statement eyewear, Hoult’s suit struck the perfect balance between rebellious and refined, because punk can, indeed, be posh.

Leslie Odom Jr. in black suit outfit and hat on red carpet at met gala
Leslie Odom Jr. Mike Coppola/Getty Images

Leslie Odom Jr., 2022

Gilded Glamour

Leslie Odom Jr.’s Fendi moment at the 2022 Met Gala was a masterclass in the power of subtle details. His short-cut coat, with unorthodox three-quarter sleeves, added a unique twist to an otherwise understated look, as did his unexpected round black hat. Odom Jr. proved that it’s the finer points that elevate an outfit from ordinary to extraordinary.

Travis Scott attends the Heavenly Bodies: Fashion & The Catholic Imagination Costume Institute Gala at The Metropolitan Museum of Art on May 7, 2018 in New York City.
Travis Scott. Getty Images for The Met Museum/

Travis Scott, 2018

Heavenly Bodies: Fashion and the Catholic Imagination

Travis Scott went for a head-to-toe black outfit by Alexander Wang  at the 2018 Met Gala. The safari-style jacket, tailored trousers, and standout leather-and-chains belt demonstrated that monochrome ensembles can, in fact, be anything but boring. Scott’s look was a lesson in making a statement without relying on color.

man in all pink outfit and sunglasses standing on red carpet
Sebastian Stan. Jeff Kravitz/FilmMagic

Sebastian Stan, 2022

Gilded Glamour

While not strictly adhering to the gilded glamour white tie theme, Sebastian Stan’s hot pink Valentino look, designed by Pierpaolo Piccioli, transformed a casual outfit into a red carpet showstopper. It’s a striking visual that confirmed some rules are meant to be broken.

man in white jacket and pants stands on red carpet
Timothée Chalamet. Theo Wargo/Getty Images

Timothée Chalamet, 2021

In America: A Lexicon of Fashion

Timothée Chalamet was one of the Met Gala’s co-chairs in 2021, and it was no surprise that he brought his fashionable A-game for the evening. The Dune star’s black-and-white look—a seamless blend of Rick Owens, Haider Ackermann, and Converse high-tops—signaled that dressed-down tailoring can be just as chic as dressed-up formalwear. The satin bomber jacket, slim-cut trousers (or glorified sweatpants), and laid-back sneakers offered a refreshing take on red-carpet fashion, proving that style and comfort can coexist.

The 15 Best Men’s Fashion Moments in Met Gala History