Frazer Harrison/Getty; Gilbert Flores/Celebrity Ph
The Matchup: Michelle Williams in Vera Wang (2006) vs. Keira Knightley in Vera Wang (2006)
Who Made the Call?: Alex Apatoff, Style News Editor
My Pick: Michelle Williams
Hear Me Out: With all due respect to Keira Knightley’s very glamorous burgundy one-shoulder gown (and the jaw-dropping Bulgari jewels that came with it), this race was over before it even started. Michelle Williams’s striking marigold number by the same designer has made countless best-dressed (and best-ever) lists since the moment Williams walked onto the red carpet. Where Knightley’s ruched taffeta confection was perfectly pretty, Williams’s was surprising (for the low-key star), bold (that yellow color!), blinged-out (those 19th century Fred Leighton diamonds!) and best of all, memorable.
Check out the full Oscars Gown Showdown bracket here!
In fact, I think all starlets should be assigned this photo to study as a master class in red carpet dressing. The dress fit her like a glove, and had just enough drama in the details to make her stand out without overwhelming her petite frame. To that end, she knew to add a bold red lip to ensure that the bright hue wouldn’t wash out her pale skin. And the hair accented the entire look perfectly — it was a little bohemian, a little romantic and not a strand was out of place.
She didn’t walk away with the Oscar for which she was nominated that year, but she did manage to secure a place in the ephemeral pantheon of best red carpet moments, so I’ll consider it a win for her anyway.
Voting is now closed but click here to see who came out on top — and to weigh in on today’s matchup: Reese Witherspoon vs. Zoë Saldana!