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The Oscars isn’t known for being the wildest or most experimental venue for men’s style: if you’ve got a tux, you’re covered. But scan the show’s 91-year history and you’ll find plenty of deep swerves from the nominees and their dates. Of course, a good number of them took place between 1970 and 1973, but ’80s had a few champs, too, and the men of the 2010s are doing their part to keep things interesting. You’ve seen the worst chances ever taken on the Academy Awards red carpet. And now, here are the best.
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Mike Coppola
Timothée Chalamet in Louis Vuitton and Cartier
Who needs a shirt?
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Barcroft Media
Mahershala Ali, 2019
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Ron Galella
Clint Eastwood, 1970
It was a time of fluffy hair and shiny suits…
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Campbell Addy
LaKeith Stanfield, 2021
Don’t call it recency bias: Stanfield’s Saint Laurent jumpsuit might be the best Oscars outfit ever.
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Ron Galella
Sammy Davis Jr., 1970
and Texas-sized collars.
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Ethan Miller
Pharrell Williams and Helen Lasichanh, 2014
Remixed black-tie, done doubly right.
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Frazer Harrison
Heath Ledger and Michelle Williams, 2006
Setting the bar on date-night style extremely high.
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Amy Sussman
Brad Pitt, 2020
Pitt’s sumptuous Brioni tux—and awesome mane—is a reminder that it’s hard to outdo the classics.
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Michael Caulfield
Christian Bale, 2011
From cargo pants, to the blackest black-tie.
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Ron Galella
Michael Jackson and Brooke Shields, 1981
No one did party clothes like 1981.
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Steve Granitz
Mark Ronson, 2019
Big fat lapel, a little flare in the pants, and a floppy ol’ tie: this is louche luxury.
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Ron Galella
Sonny Bono and Cher, 1973
A velvet tux and a big mustache. What is this, 2019?
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Amy Sussman
Timothée Chalamet
Prada and Chalamet are a match made in taking-red-carpet-risks heaven.
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Michael Ochs Archives
Paul and Linda McCartney, 1973
The bigger the collar, the closer to (style) god.
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Fotos International
Joe Namath and Raquel Welch, 1972
A football player in a powder-blue ruffled tux shirt. Now that’s sweet.
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Jason Merritt
Eddie Redmayne, 2012
King of the midnight blue tuxedos.
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Frank Worth, Courtesy of Capital Art
Bette Davis, Marlon Brando, and Grace Kelly, 1955
‘50s classic.
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Kevin Mazur
Michael B. Jordan, 2014
Solid-gold Oscars style.
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Eric McCandless
Chadwick Boseman, 2018
The beginning of menswear’s opulent phase.
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Ron Galella
Robert Redford, 1981
Here’s to bigger bow-ties and longer hair.
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Frazer Harrison
Ryan Gosling, 2017
Bringing back the ruffled tux shirt.
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Ron Galella
Daniel Day Lewis, 1990
Chalamet, eat your heart out.
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Ron Galella
Michael Caine and Nikki Caine, 1973
Coolest dad ever.
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Kevin Mazur
Jared Leto, 2014
This is how you swerve at the Academy Awards.
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Ron Galella
Jack Nicholson, 1971
Even in velvet, Jack Nicholson looks like a badass.
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Steve Granitz
Spike Lee, 2020
Lee’s purple-and-gold tux doubled as a touching tribute to Kobe Bryant, who died shortly before the 2020 Oscars.
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Kevin Mazur
Andrew Garfield in Saint Laurent and Omega
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Michael Ochs Archives
Dennis Hopper, 1970
What dress code?
