Will These Boundary-Pushing Men’s Looks End Up on the Oscars Red Carpet?

Dior Men Fall 2020

The biggest news in men’s red carpet style this year has been Joaquin Phoenix wearing the same Stella McCartney tuxedo to every awards show. He’s making a statement about waste and the unspoken absurdity of Hollywood’s wear-it-once-and-never-again rule, but here’s the thing: If he hadn’t made the announcement, we probably wouldn’t have noticed that he “repeated” his Golden Globes outfit at the Critics Choice Awards. A black tux is about as classic and formulaic as it gets, and it’s the no-brainer uniform of nearly every guy in Hollywood. We rarely expect to be surprised by their sartorial choices; it qualifies as big news if we see a jewel tone or a touch of velvet on a lapel.  
 That’s starting to change, though. First, there’s the obvious influence of young men like Timothée Chalamet, Ezra Miller, Lil Nas X, and Harry Styles, who experiment freely with fashion and are wholly unconcerned with traditional ideas about masculinity. We can say with 100% certainty that none of them will choose a basic black tux for the Screen Actors Guild Awards or the Oscars, should they attend (fingers crossed for Timmy!). By now, we’ve come to expect the unexpected from them. What would be truly surprising is if other men—namely A-list nominees like Brad Pitt and Leonardo DiCaprio—followed their younger colleagues’ leads and chose unconventional, fashion-forward looks for themselves.  
 The fall 2020 menswear collections have offered up dozens of compelling options: colorful suits at Tom Ford and Ermenegildo Zegna; lush textures at Ann Demeulemeester and Berluti; romantic ruffles at Ami and Louis Vuitton; and shocking moments of couture-like embellishments and shine at Alexander McQueen, Dior Men, and Givenchy. It’s the first time the major men’s collections have merited words like beautiful, lush, and even feminine, to the degree that calling it “menswear” feels kind of regressive. Saorise Ronan could wear Valentino’s emerald sequined suit and we wouldn’t think twice about it, but it’s a male heartthrob like Adam Driver who would make headlines for doing so.  
 Here, we’ve pulled 16 looks we’d love to see Pitt, DiCaprio, Driver, and co. try at the remaining awards shows; come back Sunday evening for our coverage of the SAGs to see if any took the risk.