Of all the events in Hollywood, the Academy Awards is home to some of the most over-the-top and flamboyant looks of all time. It’s basically the mother of all award shows, and each year our favorite celebs hit the red carpet in jaw-dropping couture that leaves us absolutely floored.
This Sunday, March 10, marks the 96th Oscars ceremony, and we can’t wait to see our favorite A-listers serving some serious looks. After all, with a rich history of shocking looks from Lady Gaga’s red gloves to Björk’s swan dress, the Oscars are pretty much a guarantee for a memorable set of looks.
Following suit with this year’s awards shows, we’re expecting the ceremony to send off this awards season with a total bang. 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 2024 Oscars tonight, see all the looks that drew stares below, some that raised the bar for fashion, and others we still just don’t get.
A version of this article was originally published in April 2021.
Gigi Hadid
Gigi Hadid proved that red is totally her color at the 2023 Vanity Fair Oscar Party in this off-the-shoulder sculpted gown by Zac Posen.
Hunter Schafer
Hunter Schafer absolutely turned heads at the 2023 Vanity Fair Oscar Party in this ivory skirt with solely a feather covering her breasts. Talk about daring!
Emily Ratajkowski
Talking about daring, Emily Ratajkowski wore this completely sheer look at the 2023 Vanity Fair Oscar Party.
Cara Delevingne
Cara Delevingne arrived at the 95th Annual Academy Awards wearing this cherry red gown from Elie Saab and it is by far one of the most breathtaking fashion moments we’ve seen this year — and possibly any year?
Allison Williams
Allison Williams did not come to play in this showstopping blush pink gown from Giambattista Valli. The dramatic train has won over our hearts, along with the Old Hollywood-style sequined dress.
Mindy Kaling
Mindy Kaling took our breath away in one of her most daring red carpet ensembles at the Oscars 2023, rocking a custom Vera Wang dress with stunning cutouts.
Timothée Chalamet
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.
Kristen Stewart
Kristen Stewart made everyone hav a double-take at the 2022 Oscars red carpet as she wore these black mini shorts, an unbuttoned white button-down and a black blazer on top.
Barbra Streisand
Barbra Streisand’s Peter Pan collar and sheer pantsuit at the 1969 Oscars (where she won Best Actress) wa decades ahead of its time.
Cher
Cher’s attire 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.
Cher (Again!)
In another head-turning look, Cher wore this skin-baring multi-colored two-piece set at the 1974 Oscars.
Demi Moore
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.
Kim Basinger
Kim Basinger made quite a splash at the 1990 Academy Awards in this one-shoulder dress with gold details and a matching glove.
Whoopi Goldberg
Whoopi Goldberg’s dress was full of surprises in 1993 including attached pants underneath the purple billowing skirt.
Kate Hudson
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!
Björk
The infamous swan dress made history in 2001 when Björk walked out in the Marjan Pejoski number that had all eyes on her.
Gwyneth Paltrow
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.
Uma Thurman
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.
Hilary Swank
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.
Tilda Swinton
While we love Tilda Swinton, this asymmetrical black velvet look at the 2008 show was a miss for many viewers. That night, Swinton won the Best Supporting Actress award for her performance in Michael Clayton.
Madonna & Lourdes Leon
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.
Angelina Jolie
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.
Lady Gaga
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!
Paris Jackson
Daughter of Michael Jackson Paris Jackson left little to the imagination when it came to her love of tattoos at the 2018 Oscars party in her bejeweled, inked-up look that drew plenty of stares.
Taraji P. Henson
Angelina who? Taraji P. Henson reinvented the slit at the 2018 Academy Awards and let her legs do the talking.
Rita Moreno
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!).
Billy Porter
Billy Porter’s 2019 Oscars look was the best of both feminine and masculine fashion and the absolute definition of formalwear.
Laura Dern
2020 Oscar-winner Laura Dern walked the 2021 Oscars red carpet in this dress featuring voluminous feathers on the skirt and a long-sleeved black top.
Gwyneth Paltrow
At the 1999 Oscars, Gwyneth Paltrow absolutely wowed in this baby pink billowing gown and matching tulle shawl. The actress went on to win the Best Actress award for her leading role in Shakespeare in Love.
H.E.R.
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!
Halle Berry
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.
Zoë Saldana
Actress Zoë Saldana wore this showstopping dégradé Givenchy gown to the 2010 Oscars. What a statement!
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