Oscars Red Carpet: The Riskiest Looks of All Time

Mermaid silhouettes, billowy princess gowns, streamlined column dresses: When it comes to red carpets, there are certain looks that are all but guaranteed. The higher-profile the event, the higher the stakes of ending up on the dreaded Worst Dressed lists, which is in part why each and every year at the Academy Awards, attendees tend to play it safe. But where’s the fun in a red carpet if no one takes any risks? Cher, Björk, Angelina Jolie, and Billy Porter are among those who’ve stepped up to the plate in recent decades, and we’re hoping more will join them when the 96th annual ceremony rolls around this Sunday. Until then, revisit the most daring looks to grace the step-and-repeat of the Oscars of all time below.

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The singer and songwriter attended her first-ever Oscars in a larger-than-life Lever Couture gown, which sparked a load of memes on Twitter when she was shown in the audience, completely blocking the view of those behind her. Tems later spoke to Harper’s Bazaar about the dress and the commotion it caused online. “Two years ago, I would’ve said no to this dress,” she said. “But it’s my first Oscars—I am going to go all out. I really wanted to make the most of the day. The dress is also my way of celebrating my work and the people around me, celebrating my country, and celebrating the people that are rooting for me. This dress says ‘Yes, yes, I am here!’”

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Kristen Stewart was definitely not the first person to wear shorts on the Oscars red carpet (see Pharrell Williams below), but she was likely the first-ever nominee of a major award to show off her legs in such a way. Usually, those up for Best Actress go for classic gowns, but Stewart is never one to follow the pack, and she opted to wear this Chanel look that is so quintessentially her.

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Men’s red carpet style has come a long way over the past few years, but it was still a bit shocking to see Timothée Chalamet show up to the Oscars in 2022 in a sequin Louis Vuitton jacket that showed off his completely bare chest. Just two years later, though, and a similar look likely wouldn’t make us bat an eye.

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Billy Porter generated so much conversation about gender norms when he turned up to the 2019 Oscars wearing a tuxedo fashioned into a gown that he later went so far to say that his custom Christian Siriano look “changed the world.”

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Pharrell Williams (seen here with his wife Helen Lasichanh)made the case for bare calves when he showed up to the 2014 ceremony wearing a Lanvin tuxedo with shorts instead of pants—a look made all the bolder by his lack of socks.

It was the leg that launched 1,000 memes. And a full decade after Angelina Jolie bared it on the red carpet, no other celebrity limb has accomplished the same since.

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We may not think of Hilary Swank baring her entire back on the red carpet as a bold move these days, but back in 2005, the actor caused enough of a stir for the Guy LaRoche design to earn its own Wikipedia page. What’s more, it doesn’t even mention half of why the dress made for some drama: Reps from Calvin Klein didn’t hide their disappointment with their brand ambassador reversing course after two weeks of talks, leading the New York Times to describe her choice of LaRoche as a “mini-scandal.”

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Björk made red carpet history when she took a swan as her plus-one to the 2001 ceremony by donning a wearable (and instantly ridiculed) version of the bird. “I don’t watch many Hollywood films, and being from Iceland, it’s pretty accidental what gets over there,” she later said when reflecting on the Marjan Pejoski design. “Most Hollywood films that I watch are Busby Berkeley musicals and—what’s that movie called with all the swimming? Esther Williams, that sort of thing, so I thought it’d be very appropriate to wear a swan. I guess they don’t do those things anymore, right? But it was a tribute to Busby Berkeley and that sort of elegance.”

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Red carpet watchers have done a 180 on how they feel about the fedora, bedazzled Ray-Bans, and backward white tuxedo by John Galliano-era Dior that Celine Dion wore in 1999. In the 23 years since, the ensemble went from at the top of pretty much every Worst Dressed list to a fan favorite.

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Lizzy Gardiner, who won 1995’s Best Costume Design award for The Adventures of Priscilla, Queen of the Desert, made chain mail fit for the present when she linked no fewer than 254 American Express credit cards (all in her name, though each missing a digit) together and declared herself fit for the red carpet. Some might call her an attention seeker, but we’d call her a comrade: Imagine trying to cobble something together amid a sea of people who have their picks of the biggest names in fashion for free. “I’m broke, and I didn’t have anything to wear,” Gardiner later recalled. “So I went through my list of past good ideas [for film costume wardrobes].”

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Cher still managed to shock when she pulled a similar move two years later, wearing more black Bob Mackie to accept the Best Actress award for Moonstruck.

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There was no missing Cher when she pulled up to the 1986 ceremony wearing a revenge dress—and revenge headdress—in the wake of the Academy snubbing her performance in Peter Bogdanovich’s Mask. “She was pissed off, because she didn’t get nominated,” Bob Mackie, the designer behind so many of her iconic looks, told the New Yorker. “There were a lot of people who said, ‘That’s not fashion!’ And I said, ‘Of course it’s not fashion. It’s a crazy getup for attention.’ And it did get attention—people talk about it still.” Case in point: He gave the interview in question a full 32 years later.

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It may look as though Akosua Busia was trying to give Oprah Winfrey some coverage with her program, but that wasn’t the issue with the ensemble that Dolly Parton’s dressmaker made for the icon. “I didn’t try the dress on,” she once recalled. “So when I went to put it on half an hour before the Oscars…I couldn’t get it over my hips.” It worked out in the end, but only because Winfrey—who asserted that she wasn’t exaggerating—rode to the ceremony “planked in the back of a limousine.”

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April 14, 1969 was a big night for Barbra Streisand, and not just because she and Katharine Hepburn both took home the Best Actress award. “That night, in my dressing room, I was choosing between two different outfits,” she told W decades later. “One was lovely, but very conservative. And then there was the pantsuit with plastic sequins. I had no idea that when the lights hit that outfit, it would become transparent!” That’s not all: Her Arnold Scaasi jumpsuit also ripped when she was on her way to collect the award.

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