Oscars Red Carpet: The 22 Riskiest Looks of All Time

Ever the trendsetter, Rihanna completely redefined maternity red carpet style when she turned up to the 2023 Oscars in a bump-baring Alaïa look with strategically placed cut-outs along her thighs. The chocolate brown dress was just one of three pregnancy looks Rihanna wore throughout the evening.

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 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!’”

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.

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.

Natalie Portman didn’t shy from calling out the Academy when she had Dior’s Maria Grazia Chiuri embroider her Dior cape with the names of the women she felt were snubbed in the 2020 Best Director category. However you may feel about their then-eligible films specifically, there’s no denying the need for outrage that the Academy has only nominated nine women—and awarded just two, Kathryn Bigelow and Chloé Zhao—over the course of what’s approaching a century.

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

Ever the risk-taker, Lady Gaga went out of her way to accessorize an Alaïa gown that would have made a statement on its own with a pair of red, rubbery leather gloves. Little did the many who made memes at the time know that seven years later, dressing ready to wash dishes (or perform surgery, for that matter) would become commonplace.

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.

Jennifer Lawrence’s elegant Dior by Raf Simons dress wasn’t first viewed as a risk when she hit the red carpet in 2013. Later in the evening, however, things took a turn. When walking on stage to accept her Best Actress trophy, Lawrence fell (rather gracefully) over her dress’s giant train. The snafu was something of a warning for future stars. While very long dresses like this photograph well, they aren’t the most practical to move around in.

Oscars gowns are usually coordinated weeks in advance, but Anne Hathaway had just minutes to decide that she would wear this powder pink Prada look in 2013. Hathaway had initially planned to wear a custom Valentino dress, but switched into this Prada number last-minute after another actor was wearing a similar outfit. To add insult to injury, Valentino mistakingly sent a press blast confirming that Hathaway would wear their design. Imagine their shock when she showed up in head-to-toe Prada. “Though I love the dress I did wear, it was a difficult last-minute decision as I had so looked forward to wearing Valentino in honor of the deep and meaningful relationship I have enjoyed with the house and with Valentino himself,” Hathaway said. “I deeply regret any disappointment caused.”

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.

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.”

Sheer might seem like a safe bet these days, but when Gwyneth Paltrow wore this see-through Alexander McQueen dress in 2002, it was quite the risk. Even now, it’s rare to see a star embrace sheer fabric on the main red carpet of the Oscars. The after-parties? A different story. “I still love the dress itself, but I should have worn a bra, and I should have just had simple beachy hair and less makeup,” Paltrow later said. “Then it would have worked as I wanted it to—a little bit of punk at the Oscars.”

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.”

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.

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].”

Whoopi Goldberg divided fashion critics at the 1993 Oscars when she wore this capri-length one-piece suit with a dramatic multi-color cape placed over top.

While actors often work with top labels for their red carpet looks for Oscars Sunday, Kim Basinger’s spliced white gown was actually of her own design. Still, the fashion world wasn’t too sure about the half-tux, half-gown look at the time.

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.

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.

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.”

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.