Known as the ‘Super Bowl of fashion,’ the Met Gala is undoubtedly the industry’s most talked about night. With big shot film stars, rising musicians, supermodels, and everyone in between making appearances, guests have historically pulled out all the stops for the grand occasion.

Too, the gala’s annual theme presents an interesting dialogue between designers and guests as they are tasked with interpreting the dressed code dictated by the Costume Institute. In the past few years, themes have included takes on Americana, odes to futurism, and dedications to designers like Miuccia Prada and Rei Kawakubo. The dress code for the 2022 interation is Gilded Glamour and will be co-hosted by Regina King, Blake Lively, Ryan Reynolds, and Lin-Manuel Miranda. ⁣

Though the gala is known for show-stopping fashion moments, male attendees have historically opted for more toned down, conventional looks, usually all-black suiting or tuxedos complete with a bow tie. Despite that, as society as a whole becomes more accepting of men exploring the experimental facets of fashion, the menswear Met Gala looks have slowly but surely come around. Over the years, men have become more comfortable taking sartorial risks on the big stage, as evidenced by the looks at the 2021 edition. The night’s theme, In America: A Lexicon of Fashion, saw stars like Jeremy Pope, A$AP Rocky, and Lil Nas X nail the dress code with beaded tailoring, flowing gold capes, and gender-bending statement pieces.

Before stars step out in their finest outfits for this year’s gala, we are taking a look back at the best dressed men over the Met Gala’s decade-spanning history. From flashy interpretations of sportswear  to sheer lace dresses that surely turned heads, these menswear outfits stepped outside the box fashion-wise. Below, see the 15 best menswear looks in Met Gala history.

Jared Leto: Camp: Notes on Fashion, 2019

Decked out in Gucci by Alessandro Michele, actor Jared Leto turned heads on the Met Gala red carpet (no pun intended.) In an outfit that will go down in history, the Moribus star rocked a deep red, diamond accented robe with an exact replica of his head as an accessory.

Jeremy Pope: In America: A Lexicon of Fashion, 2021

Hollywood actor Jeremy Pope certainly made a statement at the 2021 Met Gala with his all-white outfit by Dion Lee. The off-the-shoulder jacket, ruched pants, and elongated train were made of 100% cotton and served as an ode to and reminder of America’s fraught history with slavery. “They planted seeds of beauty,⁣ tended to fields with unspeakable strength, ⁣& harvested a kind of excellence that would outlive them for centuries. So that we could one day stand up, stretch toward the sun, & tell their story,” the actor said in an Instagram caption.

Diddy: The House of Chanel, 2005

Taking it back to the early aughts, rapper and songwriter Diddy nailed 2005’s theme: The House of Chanel. The multi-hyphenate entertainer stepped out in tailored-to-perfection suiting reminiscent of the oversized Zoot Suits sported by young Black and Latino men in the 1950s. An ode to that era and the sportswear heritage of Chanel, Diddy certainly managed to merge his ultra-cool aesthetic while remaining in line with the night’s dress code.

Marc Jacobs: Schiaparelli and Prada: Impossible Conversations, 2012

“I just didn’t want to wear a tuxedo and be boring,” designer Marc Jacobs said of his daring 2012 Met Gala outfit. Boring was the last word on our minds with Jacobs’ sheer black lace button down dress worn with a pair of white briefs underneath. Complete with diamond studded loafers, the memorable look caused quite the stir.

Chadwick Boseman: Heavenly Bodies: Fashion and the Catholic Imagination, 2018

The late actor Chadwick Boseman stole the night fashion-wise at the 2018 Met Gala with a superb all white Versace outfit. As the night’s theme explored notions of the Catholic faith, Boseman’s suit and overcoat featured elaborate gold beading and ornate detailing fit for a King.

Timothée Chalamet: In America: A Lexicon of Fashion, 2021 

Fashion phenom Timothée Chalamet looked ever-so dashing at the 2021 Met Gala wearing an all-white ensemble by Haider Ackermann. The look was a thoughtful take on American sportswear and saw Chalamet rock a satin cropped tuxedo jacket with baggy white sweatpants and, of course, high top Converse sneakers.

Cody Fern: Camp: Notes on Fashion, 2019

American Horror Story star Cody Fern brought the runway to the red carpet with an experimental look by Maison Margiela. Fern sported a deconstructed beige suit with sheer black detailing, black ruched gloves, blue heeled cowboy boots, and a sheer turtleneck that covered just below the nose. And, the actor’s impeccably styled, gelled hair helped tie the one-of-a-kind look together.

Lil Nas X: In America: A Lexicon of Fashion, 2021 

For his first Met Gala appearance, Lil Nas X certainly did not disappoint. The singer, who never shies away from a major fashion moment, stepped out in an ornate gold robe by Versace. Then, the ‘Industry Baby’ singer took off the overcoat to reveal two equally as amazing looks: a gold body armor suit and a skin tight beaded catsuit.

Alexander McQueen: AngloMania: Tradition and Transgression in British Fashion, 2006

Few better pulled off the Met Gala’s AngloMania dress code than the late British designer Alexander McQueen. Attending the event with actress Sarah Jessica Parker who also wore his designs, McQueen sported a traditional plaid outfit, of course with a hint of subversion: the pleated kilt had bustles of horse hair cascading from the bottom.

Justin Bieber: In America: A Lexicon of Fashion, 2021 

Pop heartthrob Justin Bieber nailed the oversized suiting trend, wearing an exaggerated outfit from his streetwear label Drew House to the 2021 Met Gala. The ‘Peaches’ singer paired the look with crisp white sneakers and minimal gold jewelry, helping to modernize the billowing pants and well-cut blazer.

Dapper Dan: Camp: Notes on Fashion, 2019

Fashion OG, designer, and style maven Dapper Dan got his flowers at the 2019 staging of the Met Gala, Camp: Notes on Fashion. Attending the event with Gucci, the icon rocked a red tuxedo with blue floral embroidery, black cigarette pants, and oversized sunglasses. In tandem with Gucci creative director Alessandro Michele, the designer helped to craft the rest of the Italian brand’s looks for the night seen on Karlie Kloss, Ashley Graham, Omari Hardwick, and Regina Hall. Truly a moment for the fashion history books.

Virgil Abloh: In America: A Lexicon of Fashion, 2021 

Virgil Abloh, the late designer and former creative director of Off-White and Louis Vuitton Men’s, stood out from the crowd at the 2021 Met Gala. Wearing his own designs, Abloh looked ultra-cool in a deconstructed all white suit with pleated detailing. The look was made complete with light blue gloves, a white winged hat, and a sparkling pair of angular glasses.

Jaden Smith: Rei Kawakubo/Comme des Garçons: Art of the In-Between, 2017

With his bleach-blond cutoff dreads in tow, Jaden Smith in Louis Vuitton at the 2017 Met Gala was a sartorial moment to remember. The fashionable actor and singer looked dapper in sleek black suiting, a floor-length overcoat, and streamlined heeled boots to boast.

Harry Styles: Camp: Notes on Fashion, 2019

Singer Harry Styles caused quite the commotion at the 2019 Met Gala while decked out in custom Gucci. Styles, who was also a co-chair for the momentous night, wore black heeled boots, cuffed trousers, and a sheer black blouse that fans interpreted as an ode to the ‘Free The Nipple’ movement.

A$AP Rocky: In America: A Lexicon of Fashion, 2021

A self proclaimed ‘fashion killa,’ A$AP Rocky sported a colorful patchwork quilt by ERL with a black tuxedo underneath for the 2021 gala. The multi-color quilt quickly went viral on social media and was later revealed to have been repurposed from a thrift store in California. Appearing alongside Rihanna in a show-stopping Balenciaga outfit, the pair proved they are fashion’s most stylish couple.