The Flyest Oscars Looks of All Time

The Oscars The Best Dressed Men of All Time

Getty Images

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.

  • Image may contain Timothe Chalamet Fashion Human Person Premiere Clothing Shoe Footwear Apparel and Red Carpet

    Mike Coppola

    Timothée Chalamet in Louis Vuitton and Cartier

    Who needs a shirt?

  • Barcroft Media

    Mahershala Ali, 2019

  • Ron Galella

    Clint Eastwood, 1970

    It was a time of fluffy hair and shiny suits…

  • Campbell Addy

    LaKeith Stanfield, 2021

    Don’t call it recency bias: Stanfield’s Saint Laurent jumpsuit might be the best Oscars outfit ever. 

  • Ron Galella

    Sammy Davis Jr., 1970

    and Texas-sized collars.

  • Ethan Miller

    Pharrell Williams and Helen Lasichanh, 2014

    Remixed black-tie, done doubly right.

  • Frazer Harrison

    Heath Ledger and Michelle Williams, 2006

    Setting the bar on date-night style extremely high.

  • Amy Sussman

    Brad Pitt, 2020

    Pitt’s sumptuous Brioni tux—and awesome mane—is a reminder that it’s hard to outdo the classics. 

  • Michael Caulfield

    Christian Bale, 2011

    From cargo pants, to the blackest black-tie.

  • Ron Galella

    Michael Jackson and Brooke Shields, 1981

    No one did party clothes like 1981.

  • Steve Granitz

    Mark Ronson, 2019

    Big fat lapel, a little flare in the pants, and a floppy ol’ tie: this is louche luxury.

  • Ron Galella

    Sonny Bono and Cher, 1973

    A velvet tux and a big mustache. What is this, 2019?

  • Amy Sussman

    Timothée Chalamet

    Prada and Chalamet are a match made in taking-red-carpet-risks heaven. 

  • Michael Ochs Archives

    Paul and Linda McCartney, 1973

    The bigger the collar, the closer to (style) god.

  • Fotos International

    Joe Namath and Raquel Welch, 1972

    A football player in a powder-blue ruffled tux shirt. Now that’s sweet.

  • Jason Merritt

    Eddie Redmayne, 2012

    King of the midnight blue tuxedos.

  • Frank Worth, Courtesy of Capital Art

    Bette Davis, Marlon Brando, and Grace Kelly, 1955

    ‘50s classic.

  • Kevin Mazur

    Michael B. Jordan, 2014

    Solid-gold Oscars style.

  • Eric McCandless

    Chadwick Boseman, 2018

    The beginning of menswear’s opulent phase.

  • Ron Galella

    Robert Redford, 1981

    Here’s to bigger bow-ties and longer hair.

  • Frazer Harrison

    Ryan Gosling, 2017

    Bringing back the ruffled tux shirt.

  • Ron Galella

    Daniel Day Lewis, 1990

    Chalamet, eat your heart out.

  • Ron Galella

    Michael Caine and Nikki Caine, 1973

    Coolest dad ever.

  • Kevin Mazur

    Jared Leto, 2014

    This is how you swerve at the Academy Awards.

  • Ron Galella

    Jack Nicholson, 1971

    Even in velvet, Jack Nicholson looks like a badass.

  • 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. 

  • Kevin Mazur

    Andrew Garfield in Saint Laurent and Omega

  • Michael Ochs Archives

    Dennis Hopper, 1970

    What dress code?

Related Posts