The most controversial Oscars dresses of all time

March 12, 2023 | 4:25pm | Updated

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While the Oscars celebrate the best in cinema, the awards show also features one of the most high-fashion red carpets of the year. While most celebrities choose to sparkle, shine or show some skin, others stand out thanks to their polarizing outfit choices. Here, take a look back at the most-discussed Oscars dresses of all time, from Björk’s immortal swan dress to Billy Porter’s groundbreaking tuxedo ball gown — as well as looks from Angelina Jolie, Halle Berry and more.

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In a move that ruffled the feathers of red carpet purists, Kristen Stewart showed up at the 2022 Oscars wearing custom short shorts and a matching blazer by Chanel, even leaving her sheer chiffon blouse unbuttoned to her navel.

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While Halle Berry’s pink Dolce & Gabbana gown from 2021 had artful draping and a large bow in the front, the look was upstaged by her dramatically different chopped bob. The ‘do, unevenly shorn and featuring too-short bangs, was instantly mocked on social media, though it was the “Bruised” actress who had the last laugh; the next day, Berry declared she was “just kidding”
and went back to long locks.

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Natalie Portman’s custom Dior gown at the 2020 Oscars may have been well intentioned, but it ended up sparking ire. The black-and-gold cape was embroidered with the names of female directors who were snubbed by the Academy, but Rose McGowan later called Portman’s activism “deeply offensive” and said the star does not “walk the walk,” pointing out that she only worked with one other female director besides herself and that her production company has not hired any other women to direct. Portman responded by saying that she has made an effort to prioritize working with women, and will continue to do so.

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“Pose” actor Billy Porter will forever be remembered for this boundary-breaking tuxedo dress by Christian Siriano. The fashion crowd has praised the bold outfit many times over since he hit the 2019 red carpet, but some more conservative watchers are still complaining about the gender-bending look. Thankfully, however, Porter brushes off his critics and continues to push the envelope at every turn.

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Jennifer Lawrence looked like a princess at the 2013 Oscars in a strapless Dior Haute Couture gown, complete with an elegant backwards necklace. However, the star herself proved less than graceful on the big night; more memorable than her acceptance speech for Best Actress for her role in “Silver Linings Playbook” was the fall she took climbing the stairs in her too-long gown.

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While Anne Hathaway’s Prada dress from 2013 may be the most Googled of all time, thanks to the unfortunate placement of those chest darts, it’s also one of the most contentious.

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Angelina Jolie’s Versace gown from 2012 was a simple, classic choice, but her insistence on sticking her leg out in every shot turned the actress into an instant meme.

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Charlize Theron typically wows on the red carpet, but people had a hard time seeing past the placement of the rosettes on this Dior dress she wore in 2010.

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Uma Thurman’s 2004 Oscars dress by Christian Lacroix left fans wondering where she’d left her flock of sheep.

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Two years after attending the Oscars in that iconic pink Ralph Lauren gown, Gwyneth Paltrow went for the opposite effect in this 2002 Alexander McQueen look that even the actress admitted she “should have worn a bra” with.

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Viewers felt Faith Hill’s technicolor Versace gown from 2002 was a little on the nose for someone nominated for singing “Somewhere Over the Rainbow.”

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Bjork’s 2001 Marjan Pejoski swan dress will go down in history as one of the most memorable dresses in the awards show’s history. She even went the extra step of “laying an egg” on the red carpet.

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At the 2000 Oscars, “South Park” creators Matt Stone and Trey Parker proved that red carpet apparel isn’t one-size-fits-all.

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For the 1995 Oscars, costume designer Lizzie Gardiner wore a dress made completely out of expired gold American Express cards. “I’m broke,” she explained at the time, “and I didn’t have anything to wear. So I went through my list of past good ideas.”

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Whoopi Goldberg donned a neon green and purple pant/dress combo in 1993.

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Geena Davis attended the 1992 Oscars in a ruffled minidress designed by costume designers Ruth Meyers and Bill Hargate that was very saloon girl meets prima ballerina.

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Demi Moore showed up at the 1989 Oscars in this perfectly ’80s gown/bike short hybrid that she made herself.

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Cher attended the 1986 ceremony in this ab-baring, showgirl-inspired Bob Mackie original, complete with feathered headpiece.

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Edy Williams is the undisputed queen of the controversial Oscars outfit, regularly showing up in little more than a bikini (if not straight-up nude). But her most memorable ensemble is probably the one she wore to the 1986 ceremony, consisting of some strategically placed strands of pearls and a tiny white thong.

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Barbra Streisand didn’t realize quite how sheer her Arnold Scaasi jumpsuit was when accepting her Best Actress award in 1969, accidentally giving the audience an eyeful.

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