11 Best Oscar Dresses of all Time

The secret formula for choosing the perfect Oscars gown? Well, to be quite honest, there isn’t one. There’s no specific cut, color, or amount of embellishments that will guarantee a star a spot on all the “Best Dressed” lists, or ensure that their look goes down in awards show history — we simply know a winning number when we see it. It’s a design that makes us gasp, gives us an overwhelming feeling of joy, and stays fresh in our mind for days, months, and literal years afterward.

Of course, there have been a variety of past Oscars looks that have checked all those boxes and narrowing things down to a list of a top 11 list was pretty tricky. So, which celebrities and their style choices ended up making the cut? Keep reading to see our picks for the best Oscars dresses of all time.

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Best Oscar Dresses: Grace Kelly in Edith Head, 1955

Grace Kelly won an Oscar for her performance in The Country Girl while wearing 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 updo.

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Sharon Stone in Gap and Vera Wang, 1998

It’s not technically a dress, but who can forget the time when Stone showed up at the Oscars wearing a button-down from — wait for it — Gap? Sure, she balanced things out with a Vera Wang skirt, but it was definitely the chillest fashion move to be pulled at the show — and proved that a classic white shirt is well worth the investment.

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Gwyneth Paltrow in Ralph Lauren, 1999

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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Julia Roberts in Valentino, 2001

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

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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Michelle Williams in Vera Wang, 2006

Michelle Williams wore this iconic canary yellow Vera Wang design to the Academy Awards in 2006. She paired the elegant saffron gown with an equally bold crimson lip that matched the red carpet. But her best accessory of all that evening was her boyfriend, the late Heath Ledger, who was nominated for Best Actor in Brokeback Mountain.

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Angelina Jole in Atelier Versace, 2012

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

J.Law is the queen of casual style, but she definitely showed up ready to wow 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 backward.

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Lupita Nyong’o in Prada, 2014

How could we forget this baby blue Prada number, which Lupita wore while taking home a trophy for her role in 12 Years a Slave? The Best Supporting Actress Oscar winner schooled us in how to pose in a fun, flowy dress, twirling around the red carpet and having a true princess moment.

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Lady Gaga in Alexander McQueen, 2019

She’s been known to wear meat dresses and bedazzled bodysuits, but it was serious actress Gaga who appeared at the Oscars in 2019, wearing a strapless, structured Alexander McQueen gown and a 128-carat diamond necklace last worn by Audrey Hepburn.

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Sandra Oh in Elie Saab, 2020

We experienced plenty of virtual red carpets in 2020, but prior to the pandemic (and about a month before we went inside for over a year), the Oscars gave us a nice dose of glamorous, sparkly gowns — and Sandra Oh’s was a fan favorite. The Elie Saab design featured elaborate poufy sleeves and a sweet metallic bow, securing a spot in our daydreams for life.

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