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10 Oscar Dresses That Became Iconic in the Last 20 Years

ETOnline logo ETOnline 2/23/2019 Amy Lee‍

Hollywood glamour at its finest, Oscar fashion is unlike any other. 

Stars pull out all the stops for Tinseltown's biggest night, and some dresses are so good that they go down in Oscar history. So what makes a dress iconic? 

Well, first it stands out from the rest whether it's the design, silhouette, color or the accessories it's styled with. Second, it's the response it evokes -- that jaw-dropping, OMG reaction it receives the second it debuts on the red carpet. Thus, these looks are talked about for years after. 

In anticipation of the 2019 Academy Awards on Sunday, we're revisiting the most memorable dresses worn on the Oscar red carpet in the last 20 years. 

Gwyneth Paltrow, 1999

The blonde was the epitome of classic beauty as she took home the Best Actress award for Shakespeare in Love. Paltrow stunned in a voluminous light pink taffeta ball gown by Ralph Lauren with a matching sash wrapped around her arms. Her deep-parted slicked back 'do and diamond choker necklace were the perfect finishing touch to the elegant ensemble. 

a person wearing a wedding dress: Jeffrey Mayer/WireImage © Jeffrey Mayer/WireImage Jeffrey Mayer/WireImage

Julia Roberts, 2001

America's sweetheart was a vision in this black Valentino velvet gown with ivory satin trimming. Roberts won the Oscar for Best Actress for her portrayal of Erin Brockovich. The detail of the V-neckline, peekaboo panel on the bust and trimmed tulle train proved a black dress can be anything but basic. 

a woman wearing a black dress: Terry McGinnis/WireImage © Terry McGinnis/WireImage Terry McGinnis/WireImage

Halle Berry, 2002 

Berry made history when she became the first black woman to win the Best Actress award for Monster's Ball, and her Elie Saab dress solidified her movie star status. The floral-embroidered sheer bodice was sexy yet romantic (perfectly paired with her once-signature pixie cut), complemented by a dramatic burgundy taffeta skirt. 

a woman standing in front of a flower: Steve Granitz/WireImage © Steve Granitz/WireImage Steve Granitz/WireImage

Hilary Swank, 2005 

Business in the front, party in the back! Swank turned heads in a navy blue Guy Laroche draped gown that fit her like a glove when she won her second Best Actress award for Million Dollar Baby. The long-sleeve, high-neck design was modest, but when she turned around it was a different story as her (very toned) back was exposed down to the lower waist. 

a group of people wearing costumes: Dan MacMedan/WireImage © Dan MacMedan/WireImage Dan MacMedan/WireImage

Reese Witherspoon, 2006 

The Southern belle had a fairy-tale moment in a 1955 vintage Christian Dior dress as she nabbed Best Actress for her role as June Carter Cash in Walk the Line. Funny story, Witherspoon found the gorgeous beaded gown in a boutique in Paris, which was once worn by royalty. Casual. 

a group of people posing for the camera: Frank Trapper/Corbis via Getty Images © Frank Trapper/Corbis via Getty Images Frank Trapper/Corbis via Getty Images

Michelle Williams, 2006 

Although the Brokeback Mountain star did not go home with an Oscar, the Best Supporting Actress nominee won best dressed in a saffron yellow Vera Wang dress. The bright color had everyone obsessed and still stands the test of time.

a person wearing a costume: Chris Polk/FilmMagic © Chris Polk/FilmMagic Chris Polk/FilmMagic

Angelina Jolie, 2012 

Jolie became the queen of thigh-high slits when she overtly showed off her right leg in a strapless black Atelier Versace gown. The star's pose and positioning of leg spawned a slew of memes while also giving us an iconic Oscar look. 

a woman wearing a black dress: Dan MacMedan/WireImage © Dan MacMedan/WireImage Dan MacMedan/WireImage

Jennifer Lawrence, 2013 

The actress channeled princess vibes in Dior when she won Best Actress for Silver Linings Playbook. The pale pink strapless gown boasted a voluminous skirt, that caused her to (gracefully) trip en route to the stage. Nevertheless, Lawrence was stunning and we especially love how she wore her Chopard 74-carat diamond strand necklace backwards down her back. 

a person standing in front of a curtain: Jason Merritt/Getty Images © Jason Merritt/Getty Images Jason Merritt/Getty Images

Lupita Nyong'o, 2014

A real-life Cinderella, Nyong'o was breathtaking in blue via a plunging, pleated gown by Prada and Fred Leighton diamond headband. The actress scored the Best Supporting Actress award for her breakout role in 12 Years a Slave

Lupita Nyong'o standing in front of a mirror posing for the camera: Jason LaVeris/WireImage © Jason LaVeris/WireImage Jason LaVeris/WireImage

Saoirse Ronan, 2018

The Lady Bird leading lady was pretty in pink at last year's ceremony in a Calvin Klein By Appointment strapless dress with oversized bow and matching pumps. Ronan didn't take home the Best Actress award, but she won our hearts in this absolutely darling ensemble. 

a person standing posing for the camera: Jeff Kravitz/FilmMagic © Jeff Kravitz/FilmMagic Jeff Kravitz/FilmMagic


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