The Oscars' most memorable fashion moments

Holy swan dress, it's Oscars season again. Here are 10 of the most eye-catching ensembles to grace its red carpet.

Updated September 12, 2018

The Oscars' most memorable fashion moments

Memorable Oscar Fashion

Sharon Stone in Gap and Vera Wang (1998)

Two years after wearing a Gap turtleneck to the Oscars, Sharon Stone paired one of its classic white shirts with a Vera Wang skirt. Dressed up but effortless, this is how to stylishly borrow from the boys.

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Sharon Stone's white shirt moment (Click on the pink triangle for more info)

Celine Dion in John Galliano (1999)

The red carpet doesn't get much better than Celine Dion in all her OTT glory. In 1999, Celine was nominated for Best Original Song and sported a reverse white tux with a fedora and sunglasses to match.

Celine Dion channels Prince

Björk in Marjan Pejoski (2001)

Celine's reverse tux seemed wacky in the years before Björk showed up wearing a swan as a dress. Björk even laid an egg on the red carpet. Now that’s making an entrance.

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Björk's swan

Gwyneth Paltrow in Alexander McQueen (2002)

A year after wearing a super-sweet pink gown to pick up her Academy Award for Shakespeare in Love, Gwyneth ditched the girly look (and her bra).

Gwyneth goes goth

Diane Keaton in Ralph Lauren (2004)

Annie Hall is cinematic fashion at its finest, as Diane Keaton well knows. Keaton has never given up her tomboy style – sometimes she goes subtle and other times, like in 2004, she wears gloves and a bowler hat.

Diane Keaton rocks menswear

Uma Thurman in Christian Lacroix (2004)

Uma brought Octoberfest to the Oscars back in 2004. Then again, maybe she was impersonating a pirate?

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Uma Thurman does dirndl

Michelle Williams in Vera Wang (2006)

There’s no denying that the silhouette of Michelle Williams’ dress was stunning, but the saffron hue was truly what cemented her as best dressed of the night.