Oscars 2022: The most groundbreaking Oscar outfits of all time

The red carpet is truly back with the 94th Annual Academy Awards taking place in Los Angeles on Sunday March 27th.

This year, the event returns to the Dolby Theater for the first time since the pandemic began.

Last year, the film was even shot in Union Station, the main train station in the Californian city.

While we’ve already been treated to star-studded red carpets at the Baftas and British Awards, the 94th Academy Awards will return to its usual glitzy affair after two years of pandemic-related setbacks.

Ahead of this weekend’s event, which will be attended by the likes of Zoë Kravitz and Daniel Kaluuya, we’ve rounded up some of the most groundbreaking Oscar looks of all time, from Billy Porter’s tuxedo dress to Björk’s iconic ensemble.

Cher, 1986

Cher in 1986, wearing an outfit by Bob Mackie

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Cher in 1986 in a Bob Mackie outfit


It’s an outfit hard to forget: Cher in a jeweled bralette and matching low-rise skirt, paired with a voluminous feather headpiece designed by the singer’s longtime friend and designer, Bob Mackie.

But there was more to this showgirl-inspired ensemble than meets the eye. In 2019, the “Believe” singer released a video for Fashion He explained that the look was meant to be a rebuttal to the Academy for not taking her seriously as an actress.

“I came up with the idea mostly because the academy didn’t really like me,” Cher said. “They hated the way I dressed and I had young boyfriends so they thought I wasn’t serious. So I came out and said, ‘As you can see, I have my manual on how to dress like a serious actress.'”

Celine Dion, 1999

Celine Dion at the 1999 ceremony

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Celine Dion at the 1999 ceremony


Few people could pull off a backless suit. Or rather, a suit worn inside out.

But Celine Dion did amazingly well in 1999 when she wore this optically white Christian Dior suit to the Oscars.

The loose-fitting suit hung from the singer’s shoulders, creating a backless look with a deep V. Dion paired the suit with an oversized white hat, packing even more fashion punch.

Bjork, 2001

Björk at the 2001 Oscars

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Bjork at the 2001 Oscars


When you think of controversial Oscar looks, Björk’s 2001 outfit can’t be overlooked.

The Icelandic musician arrived in a crystal-encrusted body stocking covered in white tulle in the shape of a swan, with its long neck forming a halterneck design and its beak resting on her chest.

As if that wasn’t surreal enough, Björk accessorized the look with a trail of eggs that she “laid” (i.e., dropped) as she walked the red carpet.

The dress, designed by Marjan Pejoski, became iconic, Ellen DeGeneres later wore a copy to host the 2001 Emmys, while fashion house Valentino created a reimagined version of it for one of its couture collections in 2014.

Hall Berry, 2002

Halle Berry in 2002 wearing an Elie Saab gown

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Halle Berry in 2002 in an Elie Saab dress


It’s hard to forget Halle Berry’s sheer Elie Saab gown from the Oscars in 2002, when she took home a Best Actress award for her role in the Oscars monster ballmaking her the first black woman to win in this category.

The dress had a crimson taffeta skirt and a fully sheer bodice covered in floral embroidery.

It was a bold look back then – not only because the top half was completely transparent, but also because of the unique design and detailed embroidery.

Uma Thurman, 2004

‘I wore it wrong’: Uma Thurman in 2004

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“I wore it wrong”: Uma Thurman in 2004


Uma Thurman’s look at the 2004 Oscars will certainly be remembered forever, but not necessarily for the reasons she might prefer, as the actress herself would attest.

The Christian Lacroix white dress had a tulle skirt and lace covered puff sleeves with a central blue sash.

At the time, however, the look was widely derided in the media, with critics saying it was more suited to a shepherdess or a pirate.

“It was a beautiful dress,” Thurman said InStyle magazine a few years later. “Turns out I wore it wrong.”

Trey Parker, 2000

Trey Parker, left, dressed in drag as Jennifer Lopez, and Matt Stone as Gwyneth Paltrow in 2000

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Trey Parker (left) dressed as Jennifer Lopez and Matt Stone as Gwyneth Paltrow in 2000


It wasn’t exactly a fashion moment, but it was definitely groundbreaking when South Park Co-creator Trey Parker arrived at the Oscars in a green dress modeled after an iconic Versace dress worn by Jennifer Lopez to the Grammys that same year.

Parker’s colleague and co-creator Matt Stone joined in, dressing as Gwyneth Paltrow in a pink dress modeled after the one worn by Ralph Lauren at the 1999 Oscars, when she won Best Actress for her role Shakespeare in love.

The duo later admitted they both took LSD before walking the red carpet.

Angelina Jolie, 2012

Angelina Jolie, and her leg, in 2012

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Angelina Jolie and her leg in 2012


This look wasn’t so much about Angelina Jolie’s dress as it was about her leg, which got its own Twitter account shortly after the actor walked the red carpet.

Atelier Versace’s black velvet dress was simple enough in its construction – strapless, with a structured body and a full skirt. But it was the thigh-high slit, and particularly the way Jolie intentionally exposed her leg when wearing it, that made this outfit one of the most memorable in Oscars history.

Jolie’s stance became a symbol of expression of power and authority and has since been replicated by other female actresses on the red carpet.

Anne Hathaway, 2013

Anne Hathaway in her last-minute outfit in 2013

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Anne Hathaway in her last minute outfit in 2013


It may look innocent enough, but this was one of the most controversial looks in Oscars history.

In 2013, Anne Hathaway arrived at the Oscars in a pale pink Prada dress with a halterneck and tie at the back. So far so beautiful.

However, it was later revealed that the actor only decided to wear the dress two hours before the start of the event, having previously committed to wearing a dress by Valentino, who announced it in a press release before Hathaway appeared on the red carpet – I wear Prada, not Valentino.

The uproar that ensued was so great that Hathaway was forced to apologize, which she did WWDand explained that the last-minute change was because she heard someone else was going to be wearing a dress similar to Valentino’s.

“So I’ve decided it’s best for everyone involved to change my plans,” Hathaway said in the statement. “While I love the dress I wore it was a difficult last minute decision as I was so looking forward to wearing Valentino to honor the deep and meaningful relationship I have with the house and with Valentino enjoyed myself. I deeply regret any disappointment.”

Billy Porter, 2019

Billy Porter in 2019

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Christian Siriano’s Billy Porter tuxedo dress is sure to be one for the fashion history books now. It was one of the first times someone showed up in a hybrid ensemble at the Oscars — one that combined traditional elements of men’s and women’s fashion.

It was also, quite simply, a gorgeous gown with a full black velvet skirt that swept the red carpet, topped by a sharp-cut tuxedo jacket.

Porter told me Fashion then: “We wanted to play between the male and the female. This look was interesting because it’s not drag. I’m not a drag queen, I’m a man in a dress.”

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