The 20 Most Memorable Oscars Dresses Ever

Gwyneth Paltrow, 1999

in ralph lauren

The year Gwynnie won Best Actress for Shakespeare in Love, she collected her award in this sweet princess gown that instantly made pink cool again. Yep, she was like the Elle Woods of the Oscars.


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Senior Digital Editor

We're at the tail end of a jam-packed awards season, with the grand finale—the Oscars, duh—just a few days away. We can't wait to see what our favorite nominees wear—we already know Jennifer Lawrence will step out in a breathtaking Dior, while we hope to see Lupita Nyong'o pick another brilliantly bold monochromatic gown. As for which designer she'll select—Gucci? Ralph Lauren?—that's anyone's guess.

With our pre-Academy Awards anticipation at a boiling point, we thought it a prime time to take a look back at some of the most memorable Oscars looks from years past. Click through to peep some gowns that made a major impact—for better or worse.