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

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.

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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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.

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.

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.

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.

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.

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.

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.

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.

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, 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.

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., 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, 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.

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.

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.