The biggest night in the awards season calendar, the Oscars are famous for glitz, glamour, tearful acceptance speeches and, usually, a few surprises – especially in the fashion department.

While most A-listers and industry insiders tend to play it safe with jewel-toned column gowns and black tie tuxedos, you can guarantee a handful of stars will get tongues wagging with their Academy Awards red carpet choices – and not always for the right reasons.

Ahead of this year’s ceremony on Sunday March 27, here we look back at some of the weirdest and most opinion-diving Oscars outfits of all time…

1. Cher


A year after she took home the best supporting actress award, Cher reportedly chose this scene-stealing, midriff-baring, sequin-covered, showgirl-inspired ensemble (complete with voluminous headdress) because she hadn’t been nominated for her role in Mask.

Cher later expressed regret about the look, created by legendary costume designer Bob Mackie, telling British Vogue: "I always felt a bit sad that I presented Don Ameche with his best supporting actor award in that outfit. It seemed to make him a little nervous."

2. Celine Dion

(Peter Jordan/PA)

The sort of whimsical outfit that someone like Lady Gaga could get away with these days, the John Galliano-designed backwards suit Celine Dion wore to the 1999 Oscars was widely ridiculed.

It probably didn’t help that the singer styled the white, double-breasted two-piece with sunglasses and a bizarre asymmetrical hat.

3. Bjork

(Willian Conran/PA)

Long before ‘breaking the internet’ was even a thing, in 2001 Björk was responsible for arguably the most notorious Oscars appearance of all time.

The Icelandic pop star, who was nominated for best song, turned up in a nude and white tulle swan dress by Marjan Pejoski and proceeded to ‘lay’ six ostrich eggs on the red carpet, to the amusement and/consternation of the world’s media.

4. Halle Berry

(Myung Jung Kim/PA)

Back in 2002, Halle Berry’s burgundy Elie Saab gown with a see-through mesh bodice and carefully positioned embroidery was seen by some people as a bit too risqué for a best actress nominee.

That year, Berry became the first black woman to take home the award, and now her dress is regarded as one of the most beautiful off all time.

5. Gwyneth Paltrow

(Myung Jung Kim/PA)

After many years on the best-dressed lists, Gwyneth Paltrow fell out of favour with critics in 2002 when she chose a gothy Alexander McQueen dress with a vest-style top and black skirt, plus lots of dark eye make-up.

The actor-turned-entrepreneur later admitted on Goop: "I still love the dress itself, but I should have worn a bra and I should have just had simple beachy hair and less make-up."

6. Angelina Jolie

(Ian West/PA)
(Ian West/PA)

It was the dress that launched a million memes. In 2012, Angelina Jolie posed with one leg sticking out from her thigh-slit Versace gown and the internet went into overdrive, photoshopping the leg onto all kinds of unlikely scenarios. On Twitter, #AngiesRightLeg even started trending.

7. Anne Hathaway

(Ian West/PA)

Not only was Anne Hathaway mocked for her pink Prada gown at the 2013 ceremony (critics said the bust area was a bit too ‘perky’), the best supporting actress winner was forced to apologise for her last minute decision to forgo the Valentino dress she had planned to wear because it was too similar to another celebrity’s.

8. Jennifer Lawrence

(Ian West/PA)

Fashion fans gushed over Jennifer Lawrence’s bridal-esque Dior gown in 2013, but the controversy came when the best actress winner tripped over the full skirt while ascending the stage to collect her award.

Jennifer Lawrence Falling GIF - Find & Share on GIPHY

9. Pharrell Williams

(Ian West/PA)

Music star Pharrell Williams put a decidedly casual spin on the classic black tie look in 2014 when he wore a Lanvin tuxedo jacket and bow tie with tailored shorts, plus shoes with no socks – which some red carpet watchers said was a step too far.

10. Billy Porter

(Ian West/PA)

Courting controversy in the best possible way, Billy Porter went against tradition in 2019 when he wore a dress, not a suit.

Designed by Christian Siriano, the strapless black velvet gown came with a shirt and bow tie which Porter whipped off before attending the ultra-exclusive Vanity Fair after party.

11. Sandy Powell

(Ian West/PA)

Another outfit that made headlines for all the right reasons, the white suit worn by Sandy Powell in 2020 was covered in celebrity signatures the British costume designer had collected during awards season.

The suit was later auctioned to help fund the preservation of late artist and filmmaker Derek Jarman’s cottage, fetching £16,000.