The 17 Best Oscars Red Carpet Fashion Rebels of All Time

While this batch of Oscar winners might be easier to predict than in years past, the red carpet is still sure to provide spectators with plenty of surprises. Over the decades, the Academy Awards has played host to a panoply of outrageous fashion statements. Let’s revisit some of the occasion’s most memorable sartorial shocks.

Cher marched to the beat of her own drum in various degrees of bare and bronzed skin, often (scantily) dressed by the designer Bob Mackie. Who could forget that night in 1986 when the musical legend ruffled feathers in a cage-cutout midriff and maxi skirt with gravity-defying headdress up top? Equally iconic was Björk’s Oscar entrance in 2001, when she floated in wearing a literal swan dress, laying bird eggs in her wake.

Diane Keaton turned heads in full coattails and a coordinating bowler hat, recalling a fedora-wearing Céline Dion, who for one of her own Oscar moments was outfitted in a white tuxedo whose jacket was worn back to front. Before that, Demi Moore peddled up the red carpet in spandex bike shorts with a metallic brocade train behind her. Flash-forward to Gwyneth Paltrow, in 2002, who did her part to free the nipple in a see-through Alexander McQueen. But no one in Hollywood history has a leg up on Angelina Jolie, who, in 2012, sent cameras flashing when she struck a pose in a strapless Atelier Versace gown that put a slit cut up to there on full display.