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The most daring Oscars red-carpet outfits of the last 50 years, from Prince’s hooded cape and Cher’s revealing showgirl dress, to Celine Dion’s reverse Dior tuxedo and Zendaya’s Sharon Stone tribute

From Edy Williams and Cher’s revealing looks to Billy Porter’s tuxedo gown, a dress made of Amex and Zendaya’s Sharon Stone tribute, some stars pull out all the stops for the Oscars red carpet. Photos: Getty Images, AP, EPA
From Edy Williams and Cher’s revealing looks to Billy Porter’s tuxedo gown, a dress made of Amex and Zendaya’s Sharon Stone tribute, some stars pull out all the stops for the Oscars red carpet. Photos: Getty Images, AP, EPA

  • Prince’s 1985 glittering hooded cape was so iconic it was still being copied 36 years later by H.E.R, while Whoopi Goldberg turned heads in a Disney-inspired purple-and-green look in 1993
  • Kate Winslet literally shone in Ralph Lauren, costume designer Lizzy Gardiner wore a dress made of Amex cards – and who can forget Björk’s iconic swan dress in 2001?

However exciting (or not) you found this year’s Oscars red carpet, stars have long opted to wear some of their most daring and quirky outfits to the event, with many of them going down in fashion history. We all remember Björk’s swan dress in 2001, and Billy Porter in his tuxedo gown in 2019, right? Here are some of the most memorable from the past 50 years.

1976: Diane Keaton

American actor and director Diane Keaton wore a white suit with a carnation in the lapel, striped shirt and polka dot tie to the Oscars in 1976. Photo: Getty Images
American actor and director Diane Keaton wore a white suit with a carnation in the lapel, striped shirt and polka dot tie to the Oscars in 1976. Photo: Getty Images
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Diane Keaton matched a bright white suit with a striped shirt, a polka dot tie, and a giant carnation in her lapel. And while Keaton is famous for embracing menswear now, back in the 70s, this Richard Tyler design was considered unexpected.

1977: Edy Williams

Actress Edy Williams attends the 49th Annual Academy Awards Governor’s Ball in 1977 at the Beverly Hilton Hotel in Beverly Hills, California. Photo: Getty Images
Actress Edy Williams attends the 49th Annual Academy Awards Governor’s Ball in 1977 at the Beverly Hilton Hotel in Beverly Hills, California. Photo: Getty Images

Edy Williams stole the show with this look that defies explanation. In 77, Williams opted for an almost entirely sheer gown with a bustier top attached with a jewel. She also wore sparkly underwear and yet another fur coat. Oh, and a dog.

1982: Liberace

Liberace did OTT in only the way he knew how during the 54th Annual Academy Awards in Los Angeles, California. Photo: Getty Images
Liberace did OTT in only the way he knew how during the 54th Annual Academy Awards in Los Angeles, California. Photo: Getty Images

When Liberace performed at the Academy Awards, he wore a bold look covered in beads. The more you looked at it, the more intricate it became.