The most groundbreaking Oscars outfits of all time

inally, after months of Zoom acceptance speeches and stripped-back awards ceremonies, the world will witness some real-life red-carpet action this weekend. The 93rd Academy Awards will take place on Sunday 25 April in Los Angeles.

Instead of being held at the Dolby Theatre, the ceremony’s usual home, this year’s event will be filmed at Union Station, the main railway station in the city.

But unlike other awards ceremonies that have taken place this year – the Golden Globes and the BAFTAs – the organisers of the Oscars have made it very clear that virtual attendance is not an option.

Earlier this year, Deadline published a letter sent to this year’s nominees from the show’s producers, which stated: “For those of you unable to attend because of scheduling or continued uneasiness about travelling, we want you to know there will not be an option to Zoom in for the show.

“We are going to great lengths to provide a safe and enjoyable evening for all of you in person, as well as for all the millions of film fans around the world, and we feel the virtual thing will diminish those efforts,” it continued.

Although this approach has faced some criticism, it is good news for fashion fans, who have been patiently waiting for some red-carpet glamour since the pandemic began last year.

Ahead of this weekend’s event, which will see nominees including Carey Mulligan 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

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

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

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

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

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

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

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

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’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.”