Swans, backless suits and a tuxedo dress: The most groundbreaking Oscars outfits of all time

Ahead of the Oscars on Sunday, Olivia Petter looks back at some of the most memorable red-carpet outfits in the annual award ceremony’s history

Björk, Billy Porter and Halle Berry: some of the fashion pioneers the Oscars have inspired (Getty)

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

This year, the event will return to the Dolby Theatre for the first time since the beginning of the pandemic.

Last year’s even was filmed at Union Station, the main railway station in the Californian city.

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

Ahead of this weekend’s event, which will see stars including Zoë Kravitz and Daniel Kaluuya in attendance, we’ve rounded up some of the most groundbreaking Oscars looks of all time, from Billy Porter’s tuxedo dress to Björk’s famous ensemble.

Cher, 1986

Cher in 1986, wearing an outfit by Bob Mackie (Shutterstock)

It’s an outfit that is practically impossible to forget: Cher in a jewel-encrusted bralette and matching low-rise skirt paired with a voluminous feather headpiece, designed by the singer’s long-time friend and designer, Bob Mackie.

But there was more to this showgirl-inspired ensemble than met the eye. In 2019, the “Believe” singer released a video for Vogue explaining that the look was supposed to be a rebuttal to the Academy for not taking her seriously as an actor.

“I had 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 got my handbook on how to dress like a serious actress.’”

Celine Dion, 1999

Celine Dion at the 1999 ceremony (Shutterstock)

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

But Celine Dion did it astonishingly well in 1999, when she wore this optic-white Christian Dior suit to the Oscars.

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

Björk, 2001

Björk at the 2001 Oscars (AFP/Getty)

When you think of controversial Oscars looks, Björk’s outfit from 2001 is impossible to miss.

The Icelandic musician arrived in a crystal-encrusted body stocking that was covered in white tulle shaped like a swan, its long neck forming a halter-neck design and its beak resting on her chest.

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

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

Halle Berry, 2002

Halle Berry in 2002 wearing an Elie Saab gown (AFP/Getty)

It’s hard to forget Halle Berry’s sheer Elie Saab gown from the Oscars in 2002, when she took home an award for best actress for her role in Monster’s Ball, making her the first black woman to win in the category.

The gown featured a crimson taffeta skirt and a completely sheer bodice covered in floral embroidery.

It was a bold look at the time – not just because the top half was completely see-through, but because of the unique design and detailed embroidery.

Uma Thurman, 2004

‘I wore it wrong’: Uma Thurman in 2004 (Getty)

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

The white Christian Lacroix gown featured a tulle skirt and lace-covered puffed sleeves with a central blue sash.

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

“It was a beautiful dress,” Thurman told InStyle magazine some 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 (Getty)

This was not exactly a fashion moment, but it was most definitely groundbreaking when South Park co-creator, Trey Parker, arrived at the Oscars dressed in a green gown modelled on an iconic Versace one worn by Jennifer Lopez at the Grammys in the same year.

Parker’s colleague and co-creator Matt Stone joined in the fun, dressing as Gwyneth Paltrow in a pink gown modelled on the Ralph Lauren one she had worn to the 1999 Oscars when she accepted an award for best actress for her role in Shakespeare in Love.

The duo later admitted they’d both taken LSD prior to walking the red carpet.

Angelina Jolie, 2012

Angelina Jolie, and her leg, in 2012 (Getty)

This look wasn’t so much about Angelina Jolie’s dress, but her leg, which acquired its own Twitter account shortly after the actor stepped onto the red carpet.

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

Jolie’s stance became a symbol for the 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 (Getty)

It might 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 gown that featured a halter-neck and a tie at the back. So far, so lovely.

However, it later transpired that the actor had only decided to wear the dress two hours before the event began, having previously committed to wearing a dress by Valentino, who had already sent out a press release announcing this before Hathaway appeared on the red carpet – wearing Prada, not Valentino.

The ruckus that ensued was such that Hathaway was forced to release an apology, which she did via WWD, explaining that the last-minute change was due to the fact that she’d heard someone else would be wearing a dress similar to the Valentino one.

“So I decided it was best for all involved to change my plans,” Hathaway said in the statement. “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. I deeply regret any disappointment caused.”

Billy Porter, 2019

Billy Porter in 2019 (Getty)

Billy Porter’s Christian Siriano tuxedo gown is most certainly one for fashion’s history books. It was one of the first times anyone had shown up at the Oscars in a hybrid ensemble – one that combined traditional elements of both menswear and womenswear.

It was also quite simply a beautiful gown, with a full black velvet skirt that billowed out onto the red carpet, topped with a sharply tailored tuxedo jacket.

Porter told Vogue at the time: “We wanted to play between the masculine and the feminine. This look was interesting because it’s not drag. I’m not a drag queen, I’m a man in a dress.”