Cher’s ‘f— you’ Oscars look, Angelina Jolie’s sky-high slit: iconic Academy Awards dresses

Last Updated: February 28, 2025Categories: EntertainmentBy Views: 14

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Hollywood’s biggest night for movie accolades is also a night to remember for fashion. 

Every year, Hollywood’s brightest stars gather at the Dolby Theater for the Academy Awards to honor the best performances and movies of the year. Fashion enthusiasts look forward to the event each year to see what their favorite stars will wear to the big night.

Some looks have stood the test of time, and continue to be talked about many years after they were first seen on the red carpet, whether they were worn by Cher or Nicole Kidman.

Here are some of the most memorable looks on the Oscars red carpet.

Cher and Angelina Jolie split

Cher and Angelina Jolie rocked two of the Oscars’ most iconic looks. (Getty Images; Photo by Kevin Winter/Getty Images)

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Audrey Hepburn, 1954

Audrey Hepburn at the Academy Awards in 1954

Audrey Hepburn at the Academy Awards in 1954, wearing Givenchy. (NBCU Photo Bank/NBCUniversal via Getty Images via Getty Images)

Audrey Hepburn became known as a style icon from the moment she hit her first red carpet, often admired for her minimalist, elegant and timeless style.

When the actress won her first Academy Award for her first film, “Roman Holiday,” in 1954, she accepted the award in a white lace Givenchy gown, which featured a flared skirt and was cinched in at the waist with a white belt. The look has gone down as one of the most iconic Oscars dresses of all-time, and was the beginning of the star’s close relationship with the designer.

Hurbert de Givenchy started his fashion house in 1952, with Hepburn quickly becoming his muse. Not only did she wear one of his dresses to the Oscars, but also in many of her most famous movies, including “Sabrina,” “Breakfast at Tiffany’s” and “Funny Face.”

Rita Moreno, 1962 and 2018

Rita Moreno at the Oscars then and now

Moreno wore the same dress to the Oscars in 1962 and then again in 2018. (Bettmann/Getty Images; Craig Sjodin via Getty Images)

Rita Moreno made history when she won the award for best supporting actress in 1962, for her role as Anita in the original “West Side Story,” becoming the first person of Latin descent to win in that category. 

She accepted the award in a sleeveless black dress with a black and gold skirt. Moreno wore the number again to the 2018 Academy Awards, where the new version of “West Side Story” was nominated, having slightly altered it to now be strapless, and wore it with black opera gloves.  

“This is a 56-year-old gown that I wore when I won my Oscar in 1962. This is the dress. It’s been hanging in my closet and I go and stroke it now and then. I just love — it was an amazing night,” she told People TV in 2018. “They didn’t have a red carpet then, it was so different.”

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Cher, 1986

Cher wore a black two-piece dress to the 1986 Oscars, which featured a large headpiece.

Cher wore a black two-piece dress to the 1986 Oscars, which featured a large headpiece. (Getty Images)

Cher made quite the statement when she walked out in a two-piece Bob Mackie ensemble, which featured a black jewel-encrusted bra, a low-rise skirt with slits on either side, an embroidered shawl and a huge feather headpiece.

In the 2024 documentary, “Bob Mackie: Naked Illusion,” Cher and the designer discussed how the look came together, revealing Cher approached him to design the outfit for her, as a way to get back at the Academy. Cher felt the Academy had snubbed her by not giving her a nomination for her role in “Mask,” “a movie that everyone thought I would actually win,” she said, noting, “they thought I wasn’t serious.”

“And I walked out and I said, ‘As you can see, I did receive my academy booklet on how to dress like a serious actress.’ And it was kind of my, you know, my you-know-what moment… My ‘f— you’ moment to the Academy because, you know, all you have to judge me on is my work, not my life,” she said in the documentary.

Nicole Kidman, 1997

Nicole Kidman wore an iconic yellow Dior dress to the Oscars in 2001.

Nicole Kidman wore an iconic yellow Dior dress to the Oscars in 1997. (Getty Images)

While not a nominee at the award show that year, Nicole Kidman made her mark on the red carpet at the 1997 Academy Awards, when she posed for photos alongside her then-husband, Tom Cruise, in a yellow Christian Dior dress with a high neckline, a slit up the back and embroidery on top.

The dress received mixed reviews at the time, with Joan Rivers shouting, “What an ugly dress,” while live on-air covering the red carpet for E! 

John Galliano, who designed the Dior gown, told Vogue in October 2024, that was the moment “Haute couture was introduced to Hollywood” and kickstarted the business with celebrity stylists.

“I have the one John Galliano actually fitted and made for me,” Kidman said of the dress when the runway version went on display at the National Gallery of Victoria in Melbourne in 2017. “My daughters will inherit that dress.”

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Celine Dion, 1999

Celine Dion wore a white suit to the Oscars in 1999.

Celine Dion wore a white suit to the Oscars in 1999. (Photo by SGranitz/WireImage)

Celine Dion turned heads when she walked the red carpet at the 1999 Oscars, wearing a white suit jacket, worn backwards, matching white wide-legged trousers and a pointed white hat with sunglasses.

“When I wore that look, yes it was at the Oscars, and when I wore that, everyone was wearing dresses, not pants,” she told People in June 2017. “I was the only one with pants in a backward suit from Galliano and if I would do this today it would work. It was avant-garde at the time. And it doesn’t matter, you just have to assume what you wear, you wear, and I did.”

The Grammy Award-winning artist was at the award show as a nominee in the best original song category for her song The Prayer” from the film, “Quest for Camelot.”

Bjork, 2001

Bjork wore an unforgettable swan dress to the Oscars in 2002.

Bjork wore an unforgettable swan dress to the Oscars in 2002. (Photo by Mirek Towski/FilmMagic)

Bjork stunned the world when she arrived at the 2001 Oscars red carpet wearing what has since become known as the “Swan dress.” 

The Icelandic singer posed for photos in a jewel-encrusted sheer bodysuit that covered her entire body, which also featured layers of white tulle covering her lower body, which continued up to form the swan’s neck, and ended with the head, including eyes and an orange beak, resting on her shoulder.

“Well, I did bring eggs,” she told The Sunday Times in August 2004. “Six of them that I left all over the red carpet. It was really funny, cos the lifeguards (she means security men) would pick them up and run after me with their walkie-talkies: ‘Excuse me, miss, you dropped this!’ C’ mon, you don’t bring eggs unless you want to take the piss, right? I was actually amazed at how many people thought I was serious. I didn’t mean to cause a riot!”

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Halle Berry, 2002

Halle Berry wore a red dress with floral embroidery to the Oscars in 2002.

Halle Berry wore a red dress with floral embroidery to the Oscars in 2002. (Photo by SGranitz/WireImage)

Halle Berry wowed audiences when she walked the red carpet at the 2002 Academy Awards in a red Elie Saab dress that featured a sheer top with floral embroidery, a high neckline and a long silk flowing train behind her.

The actress’ win at the 74th Academy Awards for her role in “Monster’s Ball” marked the first time a Black woman won in the best actress category in the award show’s history, adding more significance to the dress. The gown is now displayed at the Academy Museum of Motion Pictures in Los Angeles. 

“Not only will this historic @eliesaabworld gown remain in the expert care of the museum’s curators and conservators, but it will also be accessible to generations of people for whom the dress also holds meaning and forever be a reminder that all things are possible. Thank you @academymuseum!” Berry captioned an Instagram post showing the dress at the museum.

Angelina Jolie, 2012

Angelina Jolie wore a black dress with a high slit to the 2012 Oscars.

Angelina Jolie wore a black dress with a high slit to the 2012 Oscars. (Photo by Jeffrey Mayer/WireImage)

Angelina Jolie nearly broke the internet when she posed for photos at the Academy Awards in 2012 in a strapless black gown with a thigh-high slit on one side.

While posing for photos, the “Girl Interrupted” star consistently posed with her right leg poking out of the slit and her left hand on her hip. The look quickly sparked memes and other jokes to appear online, with someone even making a now-deleted Twitter account called AngiesRightLeg.

“I heard something, but I didn’t pay any attention. It’s as simple as being a woman, picking a dress you like and having a night, and not really thinking about anything else,” she told The Huffington Post in March 2012.

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Jennifer Lawrence, 2013

Jennifer Lawrence famously tripped while walking up the stairs in a white Dior ballgown.

Jennifer Lawrence famously tripped while walking up the stairs in a white Dior ballgown. (Rick Rowell Disney General Entertainment Content via Getty Images/ via Getty Images)

Jennifer Lawrence stunned in a textured strapless white Dior ballgown when she walked the red carpet at the 2013 Academy Awards.

While walking up to the stage to accept her award for best actress in a leading role for her work in “The Silver Linings Playbook,” Lawrence unforgettably stumbled while going up the stairs, joking with the audience giving her a standing ovation, “You guys are only standing up because I fell and you feel bad.”

“I was at the Oscars, waiting to hear if my name was called, and I kept thinking, Cakewalk, cakewalk, cakewalk,” she told W magazine in January 2014. “I thought, ‘Why is ‘cakewalk’ stuck in my head?’ And then, as I started to walk up the stairs and the fabric from my dress tucked under my feet, I realized my stylist had told me, ‘Kick, walk, kick, walk.’ You are supposed to kick the dress out while you walk, and I totally forgot because I was thinking about cake! And that’s why I fell.”

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Emma Stone, 2024

Emma Stone wore a pale blue dress with a peplum detail to the 2024 Oscars.

Emma Stone wore a mint-green dress with a peplum detail to the 2024 Oscars. (Photo by Rodin Eckenroth/Getty Images)

Emma Stone blew audiences away when she arrived at the 2024 Academy Awards in a strapless mint-green Louis Vuitton dress with a peplum detail above a straight skirt with a small train.

When accepting her award for best actress in a leading role for her work in “Poor Things,” Stone famously announced to the audience that the back of her dress had broken, adding “I think it happened during ‘I’m Just Ken,’” referencing Ryan Gosling’s performance of the song from the “Barbie” movie.

“Right when I came back[stage], they sewed me back in, which was wonderful,” she told reporters in the press room afterwards, per the Los Angeles Times. “I genuinely do think I busted it during, ‘I’m Just Ken.’ I was so amazed by Ryan and what he was doing, and that number just blew my mind. And I was right there, and I just was going for it, and, you know, things happen.”

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Lori Bashian is an entertainment production assistant for Fox News Digital. 

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