Happy (almost) 30th birthday to GQ’s annual Men of the Year Party. For nearly three decades years 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 mega 30th-anniversary 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.