The 10 Best Oscar Dresses of All Time

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There's no formula for how to choose the perfect Oscars dress. There's no specific color, style, or embellishments that is guaranteed to land you on "Best Dressed" lists. Our best advice to nominees? Take cues from stars from the past, dating all the way back to Grace Kelly in 1955. Here, our top ten favorite Oscars dresses of all time.

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Grace Kelly in Edith Head, 1955

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Grace Kelly won an Oscar for her performance in The Country Girl in an ice-blue gown by Edith Head. The gown, which was originally created for the movie's premiere, was cut from a bolt of $4,000 French satin and paired with a matching evening coat, a red lip, and a perfectly glamorous hairstyle.

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Gwyneth Paltrow in Ralph Lauren, 1999

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The actress took home the award for Best Actress for her performance in Shakespeare in Love while wearing a pink Ralph Lauren gown and a diamond choker by Harry Winston, which her father, the late Bruce Paltrow, later purchased for her.

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Cate Blanchett in Jean Paul Gaultier, 2000

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Blanchett’s 2000 Gaultier gown was a work of art: adorned with gold chains (complemented by perfect gold jewelry)—it looked like it was made for her.

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Julia Roberts in Valentino, 2001

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There are little black dresses, and then there’s the vintage black dress Julia Roberts wore to the 2000 Oscars. "This dress made me nervous,” Valentino himself told InStyle. “You are never sure who is going to wear what until they walk out onto the stage. That night I was in Rome, watching the Oscars live on television, and I stayed up until the wee hours of the morning to see if she wore it."

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Halle Berry in Elie Saab, 2002

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This may very well be the original naked dress. And we can’t think of anyone else who could have better launched the trend than Halle Berry (and her fabulous pixie haircut). The mesh embroidered dress is never left off red carpet best of lists.

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Hilary Swank in Guy Laroche, 2005

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You may not think it was all that when you saw it straight on, but boy were you wrong when you saw Hilary Swank’s sapphire gown from the back. Fun fact: The gown was made up of 27 (!) yards of silk jersey.

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Angelina Jole in Atelier Versace, 2012

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Yes. That dress. When good ol’ Angie stuck her right leg out from the high slit of her Atelier Versace velvet gown, history was made.

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Jennifer Lawrence in Dior Haute Couture, 2013

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J.Law may not be red carpet ready all the time, but she certainly showed up when she won Best Actress for Silver Linings Playbook in 2013. In addition to her pale blush Dior Haute Couture gown, the actress sported a Chopard 74-carat strand of 150 diamond beads, worn backwards.

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Lupita Nyong’o in Calvin Klein, 2015

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Celebrity favorite stylist Micaela Erlanger dressed Lupita Nyong’o in a 6,000 pearl custom Calvin Klein gown, which was dramatically later stolen from her hotel room following the awards. The dress was valued at $150,000.

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Ruth Negga in Valentino, 2017

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There were high expectations for what Ruth Negga would wear to the Oscar’s, and she definitely did not disappoint in a long-sleeve ruby red Valentino gown, which she paired with an Irene Neuwirth crown, ruby earrings, and an ACLU pin.

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