10 Oscar Dresses That Became Iconic in the Last 20 Years

By

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. 

Gwyneth Paltrow Oscars 1999 dress
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. 

Julia Roberts Oscars 2001 dress
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. 

Halle Berry Oscars 2002 dress
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. 

Hilary Swank Oscars 2005 dress
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. 

Reese Witherspoon Oscars 2006 dress
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.

Michelle Williams Oscars 2006 dress
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. 

Angelina Jolie Oscars 2012 dress
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. 

Jennifer Lawrence Oscars 2013 dress
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 Oscars 2014 dress
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. 

Saoirse Ronan at Oscars 2018
Jeff Kravitz/FilmMagic

Click through all of the unforgettable Oscar dresses from past years: 

Related Gallery

RELATED CONTENT:

ET Previews the 2019 Oscars Live From the Red Carpet!

Women of Wakanda: The Female Forces Behind ‘Black Panther’s Historic Oscar Push

All the Controversies Leading Up to the 2019 Oscars: From Kevin Hart to 'Bohemian Rhapsody'