If you can’t wear something outrageous to the Academy Awards, where can you wear it? Whether it’s a massive princess-inspired ball gown or drowning your body in an elegant animal, actresses have historically made bold choices on the Oscars red carpet, some of which work out and others… less so.
But, since there’s no such thing as bad press, these actresses are all winners because we’re still talking about their Academy Awards looks. From Audrey Hepburn’s lucky Givenchy gown to Björk’s bizarre bird dress, here are the most memorable moments in Oscars fashion.
Audrey Hepburn was nominated for five Oscars throughout her career, but the only one she won was Best Actress for Roman Holiday in 1954. At the ceremony, she had Givenchy take a gown Edith Heath had designed for the film and adapt it for the red carpet. According to Hepburn’s mom, the actress called the belted floral number her “lucky dress.”
Few looks are as memorable as Grace Kelly’s blue strappy silk masterpiece, also from Edith Heath, that she wore to the Oscars ceremony in 1955. Kelly took home the Best Actress Oscar for The Country Girl.
The thing that really took her look to the next level? The inclusion of those ivory gloves that just made the whole thing ooze class and elegance, of course.
Rita Moreno wore this showstopper when she accepted the Best Supporting Actress trophy for West Side Story in 1962. And she brought it out again to present at the 2018 Oscars. There were a few alterations the second time around—like changing the neckline and adding accessories—but the statement gloves were a must both times.
“The fabric is made out of Obi, which is the sash that Japanese women use in their kimonos,” Moreno told E! at the 2018 ceremony. “It’s been hanging in my closet.”
When she headed to the 1969 Oscars, Barbra Streisand donned a daring pantsuit with flared bottoms and tuxedo trimmings by Arnold Scaasi. It was a daring look, but the biggest surprise was that you could see right through it.
“I had no idea that when the lights hit that outfit, it would become transparent!” the legend later told Vanity Fair of the controversial look. Still, it brought her good luck. She won the Best Actress Oscar for Funny Girl (in a tie with Katharine Hepburn for The Lion in Winter).
Unlike Streisand, Cher was always in barely-there clothing and she brought her bold fashion sense to the 1988 Oscars. For the biggest night in Hollywood, the Moonstruck star wore a jaw-dropping Bob Mackie gown to collect her Best Actress trophy. This sheer look with black netting and jewels in all the right places is one for the record books.
“Cher’s the eternal 15-year-old who’s going to do exactly what her mother says not to do,” Mackie later told The Hollywood Reporter of the look. “She’d been in a lot of movies where she was wearing jeans and T-shirts and hadn’t worn a getup in a long time. I said, ‘But you can’t wear that to the Academy Awards.’ She said, ‘I don’t care. I don’t want to look like a housewife in an evening gown.'” And she certainly did not.
Thelma & Louise star Geena Davis attended the 1992 Oscars as a nominee, along with her co-star Susan Sarandon. But she also took the opportunity to make a daring fashion statement with this mullet-esque Bo Peep dress from Bill Hargate.
“She was going for something with a sense of humor and different from everyone else,” Mary Ellen Fields, an associate of Hargate, told The Hollywood Reporter years later. “We were looking at a lot of magazines, ‘What if we did something like this?’ Like, ‘Wow, this is fun. We get to go to a big party and play dress-up.'” Well, “fun” is one word for it.
There are few dresses that have been as equally praised and abhorred as Nicole Kidman’s Christian Dior gown from the 1997 Oscars. Joan Rivers certainly fell into the latter category. The fashion critic made vomit noises in Kidman’s direction on the red carpet.
Kidman must have known opinions would be split. “I love it. I don’t know if people will get it,” she told The Hollywood Reporter on the carpet. “But if they don’t, well, maybe they should.” One thing’s for sure: People are still talking about it.
Céline Dion was the definition of cool at the 1999 Oscars in a backwards Dior tuxedo, pointy top hat, and diamond-studded sunglasses. She was there to perform “The Prayer” from Quest for Camelot alongside Andrea Bocelli.
Looking back, she realizes the look was ahead of its time. “When I wore that, everyone was wearing dresses, not pants,” she told People years later. “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.” That’s the attitude!
If it was a princess moment Gwyneth Paltrow wanted, that’s exactly what she got at the 1999 Oscars with her now-iconic bubblegum-pink Ralph Lauren gown.
“I just wanted to look very sweet,” Paltrow told InStyle of the outfit she wore to accept her Best Actress Oscar for Shakespeare in Love. Mission accomplished!
Chances are when you think of the most memorable Oscars fashion, you see Björk’s conversation-starting swan dress. The feathery look from Marjan Pejoski enveloped the Icelandic singer, who was a 2001 nominee for Best Original Song (for “I’ve Seen It All” from Dancer in the Dark). If the dress itself wasn’t enough to make jaws drop, Björk took it to the next level as she dropped actual ostrich eggs behind her.
“The swan dress was actually part of my winter 2001-2002 collection and Björk saw it and loved it,” Pejoski told The Hollywood Reporter later. “Björk was definitely outside the box. Without people like her, it would be boring. … Look at us, 15 years later and we’re talking about it.”
Julia Roberts rocked this stunning vintage black-and-white Valentino dress to accept the 2001 Best Actress Oscar for Erin Brockovich. It took our breath away, and the designer’s as well.
“I have dressed so many people but I have to be sincere, the person that made me feel so very, very happy was Julia Roberts,” designer Valentino Garavani later said, according to Vogue U.K. “I watched it on television and really, I was so excited that she appeared in my dress.”
Halle Berry turned many heads with an Elie Saab number that was sheer on top with an embroidered bodice and a merlot taffeta skirt at the 2002 Oscars.
But the look really stays with us because it was a history-making night. She was the first black woman to win the Oscar for Best Actress—thanks to her work in Monster’s Ball—and she gave quite the moving speech to mark the occasion.
Angelina Jolie wowed in a black Atelier Versace dress at the 2012 Oscars, but a certain body part literally stood out: her right leg. Jolie strutted the red carpet with the now-famous limb bare for all to see and it wasn’t long before she went viral.
But the actress—who was there to hand out the screenplay awards—didn’t really care what we thought. “I honestly didn’t pay attention to it,” Jolie told HuffPost. “It’s as simple as being a woman, picking a dress you like and having a night, and not really thinking about anything else.” Well, we’re all still thinking about it, Angie.
Not only does Jennifer Lawrence’s 2013 Oscars dress have the distinction of being the most expensive of all time— worth a staggering $4 million—but it’s one of the most talked-about gowns too.
That’s all thanks to a fall she had in the giant Dior gown when walking up to the stage to accept her Best Actress trophy for Silver Linings Playbook. Never has a slip-up looked so good.
One of the most angelic Oscars looks of all time is Lupita Nyong’o’s blue Prada dress from the 2014 ceremony. The gown—which she paired with a tiara-like headband—made her look absolutely regal. It really was a fairytale night for the actress, who took home the award for Best Supporting Actress for her big screen debut in 12 Years a Slave.
Nyong’o told Extra her gown was inspired by “champagne bubbles because [they] wanted to celebrate this wonderful occasion.” And the gorgeous color also reminded her of her hometown in Nairobi. And for more Oscars history, check out 19 Oscar Records You Will Not Believe.
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