Let’s face it: The red carpet dresses that make their debut at the Oscars are just as important as the award show itself. Half the fun of any award show is watching actors and actresses make their way down the carpet, give witty responses to interviewers and talk about who they’re wearing so we can dissect their decisions and praise the right ones.
Red carpet attire gives actors an opportunity to express a different side of themselves. My way of measuring how unforgettable a dress involves a combination of factors: Does the dress have a wow factor? Do the hair, makeup, and accessories compliment the dress? Was it a big moment in the actress’ career (increasing the longevity of the dress in the minds of viewers)?
Here are my top 20 Oscars dresses from the past 30 years that I believe have either made or will make red carpet history.
1. Björk in Marjan Pejoski at the 2001 Academy Awards. This dress definitely has the wow factor but it doesn’t have much else. The reason this dress will go down in red carpet history is that it’s one of the most baffling dresses ever worn to the Academy Awards. Björk was so dedicated to this look that not only did she wear this boundary-pushing swan dress but she even dropped golden eggs on the red carpet.
2. Lupita Nyong’o in Prada at the 2014 Academy Awards. The actress stunned in this pale blue Prada gown with a plunging neckline, creating her very own Cinderella moment. Not only did she pick up a Best Supporting Actress Oscar for 12 Years A Slave but she also looked like she stepped right out of a fairytale. The consensus on this dress was clear when Nyong’o made it on almost every best-dressed list.
3. Sharon Stone in Vera Wang at the 1998 Academy Awards. Stone turned heads in 1998 with a lavender satin Vera Wang evening skirt and a white button-down shirt from the Gap. The best part? The Gap shirt had been taken right out of her then-husband Phil Bronstein’s closet!
4. Hilary Swank in Guy Laroche at the 2005 Academy Awards. This number is almost as memorable as Hilary Swank’s performance in Million Dollar Baby. Swank seemed to sense she would be taking home the Best Actress Oscar when she pulled out the perfect dress for the big night. The gown, comprised of 27 yards of navy blue silk jersey, was conservative in the front with long sleeves and a high neck but unforgettable from the back.
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