This Sunday, March 15, is the 98th annual Academy Awards ceremony, and while we’re tuning in to see which films and stars win big, we’re also there to spot who will make best and worst dressed lists at the 2026 Oscars.
Oscars fashion is typically black tie and classic, but every now and then, a celebrity goes all out with a bold, head-turning look. Some of this year’s nominees, like Timothée Chalamet and Teyana Taylor, are no strangers to experimenting with fashion, but will they outdo any of the iconic looks on this list?
The Oscars have a rich history of shocking looks from Lady Gaga’s red gloves to Björk’s swan dress, and pulling a bold look at the Oscars means you’re almost guaranteed to go down in fashion history.
In that spirit, we’re taking a look back at some of the most outrageous red carpet looks through the years — the good, the bad, and the huh? — and there are fashion highs and lows we’ll never forget, from Angelina Jolie’s high-slit Versace gown to Cher’s, well, everything.
Ahead of the 2026 Oscars this weekend, see all the looks that drew stares below, some that raised the bar for fashion, and others we still just don’t get.
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Angelina Jolie (2012)
Image Credit: Donato Sardella/WWD/Penske Media via Getty Images While this wasn’t the first Oscars ceremony Angelina Jolie attended with ex Brad Pitt, it may have been the one that cemented them as power couple Brangelina — and this slit definitely made that happen in 2012.
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Lady Gaga (2015)
Image Credit: Steve Granitz/WireImage Lady Gaga’s 2015 Oscars look was quite divisive, some fans thought her giant red gloves looked more like Mr. Clean than movie star glam. If you ask us, it’s just Gaga being the fashion risk-taker she’s always been!
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Emily Blunt (2024)
Image Credit: Gilbert Flores/Variety Emily Blunt’s champagne-color Schiaparelli gown at the 2024 Oscars was something of an optical illusion thanks to its floating straps.
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Whoopi Goldberg (1993)
Image Credit: Kevin Mazur/WireImage Whoopi Goldberg’s dress was full of surprises in 1993 including attached pants underneath the purple billowing skirt.
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Kim Basinger (1990)
Image Credit: Ralph Dominguez/MediaPunch via Getty Images Kim Basinger made quite a splash at the 1990 Academy Awards in this one-shoulder dress with gold details and a matching glove.
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Kristen Stewart (2022)
Image Credit: Jeff Kravitz/FilmMagic Kristen Stewart made everyone have a double-take at the 2022 Oscars red carpet when she wore these black mini shorts, an unbuttoned white button-down and a black blazer on top.
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Hunter Schafer (2023)
Image Credit: Alberto Rodriguez/Variety via Getty Images Hunter Schafer absolutely turned heads at the 2023 Vanity Fair Oscar Party in this ivory skirt with solely a feather covering her breasts from Ann Demeulemeester. Talk about daring!
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Céline Dion (1999)
Image Credit: SGranitz/WireImage Céline Dion has always been a cool girl, and her look at the 1999 Oscars proves it.
The look consisted of a white John Galliano jacket with an open-back, white wide-leg pants and a statement asymmetrical hat.
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Timothée Chalamet (2022)
Image Credit: Gilbert Flores for Variety Dune star Timothée Chalamet’s shirtless look (and occasional tendency to flip off the camera) certainly caught viewers’ attention on the 2022 Oscars red carpet.
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Nicolas Keppens (2025)
Image Credit: Gilbert Flores/Penske Media Belgian director Nicolas Keppens took one of the characters from his Oscar-nominated short Beautiful Men as his plus one in 2025.
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Rihanna (2023)
Image Credit: Gilbert Flores/WWD via Getty Images At the 2023 Oscars, Rihanna pushed the envelope in Oscars pregnancy fashion when she showed up to the red carpet in this black leather Alaïa dress with sheer panels and cutouts covering her behind.
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Björk (2001)
Image Credit: Mirek Towski/FilmMagic The infamous swan dress made history in 2001 when Björk walked out in the Marjan Pejoski number that had all eyes on her.
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Billy Porter (2019)
Image Credit: Dan MacMedan/Getty Images Billy Porter’s 2019 Oscars look was the best of both feminine and masculine fashion and the absolute definition of formalwear.
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Halle Berry (2002)
Image Credit: Steve Granitz/WireImage Speaking of winners’ looks, Halle Berry wore this iconic dress when she won her Best Actress Award for her role in Monster’s Ball in 2002. Berry, who became the first woman of color to win in the category, dared in this sheer dress with floral appliqués and a billowing maroon skirt.
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H.E.R. (2021)
Image Credit: ABC via Getty Images In the 2021 Oscars, H.E.R. won her first Oscar for her song “Fight for You” in Judas and the Black Messiah. For the big event, she wore this showstopping bright purple bedazzled jumpsuit with a cape detail. So stunning!
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Madonna & Lourdes Leon (2011)
Image Credit: Gregg DeGuire/FilmMagic Madonna is no stranger to shocking the cameras on a red carpet, but her 2011 look was double trouble — thigh-high slits and lace, plus the appearance of then 14-year-old daughter Lourdes Leon.
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Hilary Swank (2005)
Image Credit: Donato Sardella/WWD/Penske Media via Getty Images Hilary Swank was a million-dollar lady at the 2005 Academy Awards in a backless gown that left her fans swooning. She went on to win her second Oscar that night for Million Dollar Baby.
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Uma Thurman (2004)
Image Credit: Donato Sardella/WWD/Penske Media via Getty Images While Uma Thurman is a fashion icon now, this white flowy dress with gold details and a bright blue belt she wore to the 2004 Oscars had fans raising their eyebrows.
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Gwyneth Paltrow (2002)
Image Credit: Steve Granitz/WireImage Before the naked dress trend was even invented, Gwyneth Paltrow dared to wear this black dress with a billowing skirt and a sheer top at the 2002 Oscars. Plus, the gothic makeup really pulled it all together.
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Barbra Streisand (1969)
Image Credit: Bettmann Archive Barbra Streisand’s Peter Pan collar and sheer pantsuit at the 1969 Oscars (where she won Best Actress) was decades ahead of its time.
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Cher (1986)
Image Credit: Bettmann Archive Cher’s outfit at the 1986 Academy Awards can only be described as daring from head to toe. When the wig is bigger than the rest of the outfit, that’s really saying something.
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Cher (1974)
Image Credit: Ron Galella Collection via Getty In another head-turning look, Cher wore this skin-baring multi-colored two-piece set at the 1974 Oscars.
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Demi Moore (1989)
Image Credit: Jim Smeal/Ron Galella Collection via Getty Images Demi Moore went where so few women have gone before at the 1989 Oscars: bike shorts on the red carpet. And you know what? She rocked it.
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Kate Hudson (2001)
Image Credit: Steve Granitz Archive 1/WireImage While Kate Hudson has rocked many incredible looks in her movies, including Andie Anderson’s iconic yellow dress in How to Lose a Guy in 10 Days, this look of hers at the 2001 Oscars felt plucked from a 1920s movie and we were obsessed!
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Lizzy Gardiner (1995)
Image Credit: Ted Dayton/WWD/Penske Media via Getty Images Lizzy Gardiner made history in 1995 when she showed up to the Oscars in this custom dress made up of 254 gold Amex Cards. She won the Oscar that night for Costume Design in Adventures of Priscilla, Queen of the Desert.
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Rita Moreno (2018)
Image Credit: Steve Granitz/WireImage Rita Moreno proved that being an outfit repeater pays off at the 2018 Oscars as she stunned in the same dress she first wore to the Oscars in 1962 (the same year she won the Oscar for West Side Story!).
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Zoe Saldaña (2010)
Image Credit: Bob Riha, Jr./Getty Images Actress Zoe Saldaña wore this showstopping ombré Givenchy gown to the 2010 Oscars. What a statement!