Winning an Oscar is a historic moment, and the photographs taken that night will last a lifetime, so the last thing anyone wants to be remembered for is a questionable ensemble or messy hair — looking at you Casey Affleck! So regardless of their odds the nominees really should put their best foot forward because you never know when an upset might happen.
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For example, remember Marcia Gay Harden (“Pollock,” 2000)? Few were expecting her to take Best Supporting Actress that year for her role as artist Lee Krasner — “Almost Famous” breakout Kate Hudson was the favorite — but she showed up dressed to win and made a stunning impact.
We look back at those Oscar winners who should’ve thought through their outfits a little more because many haven’t had a second chance to redeem themselves. Some of these looks were problematic in and of themselves, while others were susceptible to wardrobe malfunctions (Jennifer Lawrence nearly toppled over in her voluminous gown). But either way these champs got the last laugh, because the most important accessory is a golden trophy in hand. Check out our gallery above and see if you agree with our picks.
UPDATED: Oscar odds in all 24 categories
According to Gold Derby’s exclusive odds a week from Sunday, Emma Stone (“La La Land”) is predicted to win Best Actress and Viola Davis (“Fences”) is expected to take home the Best Supporting Actress trophy. Both of these previous nominees have shown in the past that they know how to dress to win; let’s home they remember that this year.
Make sure to check out our other Oscar galleries:
Every Oscar winner for Best Picture
Every Oscar winner for Best Actor
Every Oscar winner for Best Actress
Every Oscar winner for Best Supporting Actor
Every Oscar winner for Best Supporting Actress
Musicals that won Best Picture
Westerns that won Best Picture
9 Actors Who Won Tony and Oscar for the Same Role
Which Actors Earned Oscar Nominations for Musicals?
Which Actresses Earned Oscar Nominations for Musicals?
Tom O’Neil: My Top 25 Oscar Best Picture Winners of All Time
Predict the Oscar winners now; change them until February 26
Be sure to make your Oscar predictions. Weigh in now with your picks so that Hollywood insiders can see how their films are faring in our Oscar odds. You can keep changing your predictions right up until just before winners are announced on February 26 at 5:00 pm PT/8:00 pm ET. And join in the fierce debate over the Oscars taking place right now with Hollywood insiders in our forums.
