From Denzel Washington and Jacob Elordi to Rihanna and Bill Nye (!), these are the biggest, swerviest, most unforgettable ensembles from menswear’s biggest night through the ’90s, 2000s, and today.Photographs: Getty Images; Collage: Gabe ConteIt’s the best time of the year: GQ’s annual Men of the Year Party. For three-plus decades and counting, November in Los Angeles has been punctuated by the starriest, most show-stopping event of the season. (Actually, there have been a few exceptions—like MOTY 2002, which honored that year’s magazine cover stars Denzel Washington, Hugh Grant, and Ralph Lauren—that took place in New York City. As an event, it’s sort of spiritually bicoastal.) And when we’re talking about the biggest menswear red carpet of the year, let’s just say that “big menswear” has meant a lot of different things through the high-octane 1990s, the freaky-deaky early aughts, the buttoned-up 2010s, and the no-rules 2020s.With the latest iteration of the Men of the Year bash just around the corner, we’re taking a look back at a smattering of the biggest, boldest looks to ever strut the MOTY red carpet, from OutKast’s galactic-level fits in ’02 to Dwayne Johnson’s take on the post-WWE modern cowboy in 2024.Which burgeoning style icons will earn their rightful place in this hall of fame this year? Keep a close eye on GQ.com this month to find out.ExpandEvan Agostini / Getty ImagesLenny Kravitz, 1999🎶 I want to get away / I want to flyyy awayyyy 🎶ExpandGilbert Flores/Getty ImagesMegan Thee Stallion, 2023Absolutely.ExpandMark Mainz / Getty ImagesAdrien Brody, 2003Would you look at that swoop of hair!ExpandMichael Buckner/Getty ImagesOscar Isaac, 2025Was Oscar Isaac born to wear this Tom Ford suit? Scientists want to know.ExpandJon Kopaloff / Getty ImagesRobert Pattinson, 2017Remember the air tie? Those were the good days.ExpandRon Galella / Getty ImagesBeyoncé, 2003MOTY is all about pulling up in style.ExpandAxelle/Bauer-GriffinShaboozey, 2024The first and only “Man of the Year” sash we've ever seen on the MOTY carpet.ExpandRodin Eckenroth / Getty ImagesTom Holland, 2021Sheesh!ExpandAmy Sussman/Getty ImagesHailey Bieber, 2025ExpandSteve Eichner / Getty ImagesSteven Spielberg and Gwyneth Paltrow, 1999There's nothing wrong with re-wearing your Oscars tux.ExpandGilbert Flores/Getty ImagesJacob Elordi, 2023From now on, let's refer to the color combo of this custom Bottega Veneta suit as “charcoal lemonade.”ExpandJon Kopaloff / Getty ImagesSnoop Dogg, 2017Nothing can touch Snoop's elegance.ExpandPhillip Faraone / Getty ImagesTroye Sivan, 2021Business on top, “Rush” on bottom.ExpandLester Cohen / Getty ImagesRihanna, 2012Has Rihanna ever not been in her bad-gal era?ExpandRon Galella / Getty ImagesJennifer Lopez, 1998Tweed has never looked this slinky since.ExpandLeon Bennett / Getty ImagesQuavo, 2021Mixed greens.ExpandPatrick McMullan / Getty ImagesOmarion, 2010With a Louis Vuitton-monogrammed fur sash under the suit jacket? There are levels to this.ExpandFrazer Harrison/Getty ImagesKim Kardashian, 2023Nothing screams GQ more than the phrase “custom Chrome Hearts.”ExpandRon Galella / Getty ImagesIman, 1997The one and only Iman, looking élégante as always.ExpandMichael Buckner / Getty ImagesLeonardo DiCaprio, 2008A nice velvet suit moment from Leo.ExpandAxelle/Bauer-GriffinDwayne Johnson, 2024Yeehaw!ExpandStefanie Keenan / Getty ImagesJulia Fox, 2019Hot on the heels of Uncut Gems, Julia Fox had arrived.ExpandKevin Winter / Getty ImagesUsher, 2004ExpandJim Spellman / Getty ImagesAndrew Lauren, Ralph Lauren, Ricky Lauren, Dylan Lauren and David Lauren, 2002A true-blue American dynasty.ExpandFrazer Harrison/Getty ImagesTom Ford, 2023The one, the only.ExpandMichael Buckner / Getty ImagesZac Efron, 2008He had his head in the game with this all-black ensemble.ExpandCarmen Valdes / Getty ImagesOutKast, 2002Gold quilted trousers, oversized prom-king tux, can't lose.Sign up for Show Notes to get news on the latest runway shows, parties, and insider events on the international fashion circuit.Stories from the editors of GQ. ... Read More
The 73 Best-Ever Celebrity Fits From Every GQ Men of the Year Party
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