Cher's 'F You' Oscars Look & Angelina's Sky-High Slit: Iconic Academy Awards Dresses

Hollywood's grandest night for celebrating cinematic achievements is equally renowned for its unforgettable fashion moments. Each year, the Dolby Theater becomes the stage for the Academy Awards, where Hollywood's brightest stars gather to honor the year's best performances and films. Fashion enthusiasts eagerly anticipate this event, keen to witness the sartorial choices of their favorite celebrities.

Certain looks have transcended time, remaining iconic and sparking conversations long after their red carpet debut, whether adorned by Cher or Nicole Kidman. Here's a glimpse into some of the most memorable ensembles to grace the Oscars red carpet.

Audrey Hepburn established herself as a style icon from her initial red carpet appearance, consistently admired for her minimalist, elegant, and timeless aesthetic. In 1954, when she received her first Academy Award for "Roman Holiday," she donned a white lace Givenchy gown, featuring a flared skirt cinched at the waist with a white belt. This look is celebrated as one of the most iconic Oscars dresses ever and marked the beginning of her close collaboration with the designer.

Hurbert de Givenchy launched his fashion house in 1952, with Hepburn quickly becoming his muse. She wore his designs not only at the Oscars but also in numerous iconic films, including "Sabrina," "Breakfast at Tiffany's," and "Funny Face."

Rita Moreno made history in 1962 when she won Best Supporting Actress for her role in the original "West Side Story," becoming the first Latina to win in that category. She accepted the award in a sleeveless black dress with a black and gold skirt, which she reprised at the 2018 Academy Awards, where the new "West Side Story" was nominated. She slightly altered the dress to be strapless and paired 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."

Cher made a bold statement in a two-piece Bob Mackie ensemble, featuring a black jewel-encrusted bra, a low-rise skirt with slits, an embroidered shawl, and a dramatic feather headpiece. In the 2024 documentary "Bob Mackie: Naked Illusion," Cher revealed she commissioned the outfit as a response to feeling snubbed by the Academy for her role in "Mask."

"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. Gotta respect Cher for owning that moment; it's pure diva energy.

Nicole Kidman, though not a nominee in 1997, made a splash in a yellow Christian Dior dress with a high neckline, a slit up the back, and embroidery. Despite mixed reviews, with Joan Rivers famously calling it "an ugly dress," John Galliano, the designer, considered it the moment haute couture entered Hollywood.

"I have the one John Galliano actually fitted and made for me," Kidman said of the dress when the runway version went on display in 2017. "My daughters will inherit that dress."

Celine Dion raised eyebrows at the 1999 Oscars, wearing a backwards white suit jacket, matching 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 2017. "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."

Bjork shocked the world at the 2001 Oscars, arriving in the infamous "Swan dress." The Icelandic singer wore a jewel-encrusted sheer bodysuit with layers of white tulle forming the swan's neck and head resting on her shoulder. She even brought eggs, leaving them on the red carpet.

Halle Berry stunned at the 2002 Academy Awards in a red Elie Saab dress with a sheer, floral-embroidered top and a long silk train. Her win for "Monster's Ball" marked the first time a Black woman won Best Actress, adding significance to the dress, now displayed at the Academy Museum of Motion Pictures.

Angelina Jolie nearly broke the internet at the 2012 Academy Awards in a strapless black gown with a thigh-high slit. Her poses, consistently featuring her right leg, sparked memes and a Twitter account dedicated to "AngiesRightLeg." She told The Huffington Post, "It’s as simple as being a woman, picking a dress you like and having a night, and not really thinking about anything else." That leg deserved its own agent, tbh.

Jennifer Lawrence stunned in a white Dior ballgown at the 2013 Academy Awards but stumbled while accepting her award. Joking with the audience, she said, "You guys are only standing up because I fell and you feel bad."

Emma Stone wowed at the 2024 Academy Awards in a mint-green Louis Vuitton dress but revealed her dress broke during Ryan Gosling's "I'm Just Ken" performance. "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," she said.