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The Sexiest Oscars Dress From Each Decade

We still haven’t moved on from Cindy Crawford in 1991.

Women By

For 90 years, through memorable roles and unforgettable wardrobes, these women have redefined what sexy even means to the collective American consciousness. This year, Taraji P. Henson’s custom Vera Wang gown completely stole the show. 

Taraji P. Henson attends the 90th Annual Academy Awards. (Frazer Harrison/Getty Images)

Below are the sexiest dresses from Oscars history. Do you agree with our list?


Mary Pickford was a pioneer in the silent film era, defining “movie star” for millions in beloved classics like Stella Maris, My Best Girl and Pollyanna. She is the second woman to win a Best Actress Oscar in 1931 for her work in her first film with sound, Coquette.

Mary Pickford (Alice S. Hall/NBC/NBCU Photo Bank via Getty Images)


Vivien Leigh nabbed her first of two Oscars in 1940 for her iconic portrayal of Scarlett O’Hara in Gone With the Wind.

Vivien Leigh proudly holds her Best Actress Oscar on March 2, 1940. She was recognized for her portrayal of Scarlett O’Hara in Gone With the Wind. (Getty Archives)


Vikki Dougan was a 1950s “It” girl and she made sure everyone knew it when she attended the Academy Awards with Manning Ross in March of 1957. It’s clear why she’s the real-life inspiration for Jessica Rabbit — and the stunning backless attire for which she became known was scandalous for its time.

Model Vikki Dougan and Manning Ross at the 1957 Oscars (Earl Leaf/Michael Ochs Archives/Getty Images)


Ava Gardner was considered Hollywood’s most irresistible woman, and Tinsel Town’s top men thought so, too: She was married and divorced to the likes of Mickey Rooney, Artie Shaw and Frank Sinatra.

Actress Ava Gardner wears a tiara and an evening gown as she sits in her seat in the audience of the Academy Awards ceremony which she held at the RKO Pantages Theatre on April 4, 1960, in Los Angeles, California. (Frank Worth, Courtesy of Capital Art/Getty Images)


Dinosaurs aside, Raquel Welch made One Million Years B.C. look like an all-around pretty appealing place to be. Here she’s pictured on  Gene Hackman’s arm with Best Supporting Actress Cloris Leachman at the 1972 Oscars.

Actors (L-R) Raquel Welch, Gene Hackman and Cloris Leachman (holding her Best Supporting Actress Oscar) at the 44th Academy Awards in Hollywood, CA, April 17, 1972. (Keystone/Hulton Archive/Getty Images)


In 1988, singer Cher took home an Oscar for her performance in “Moonstruck.” No one remembers that movie, but everyone remembers this dress.

Singer/Actress Cher attends the 60th Annual Academy Awards on April 11, 1988, at Shrine Auditorium in Los Angeles, California. (Ron Galella/WireImage)


Pictured with then-boyfriend Richard Gere at the 63rd Academy Awards, model Cindy Crawford didn’t exactly need help turning heads, but that’s exactly what this Versace dress did in 1991.

Richard Gere and Cindy Crawford during 63rd Annual Academy Awards at Shrine Auditorium in Los Angeles, California, United States. (Ron Galella/WireImage)


Jennifer Lopez is a multi-talented, timeless beautiful who is stunning regardless of the decade. This shot of her in a pale pink Versace dress at the 2002 Oscars is particularly memorable, though.

Actress Jennifer Lopez poses backstage at the 74th Annual Academy Awards held at the Kodak Theatre in Hollywood, Ca., March 24, 2002. (Frank Micelotta/GettyImages)


Sometimes, pictures don’t need captions. This is one of those times.

Actress Angelina Jolie arrives at the 84th Annual Academy Awards held at the Hollywood & Highland Center on February 26, 2012, in Hollywood, California. (Ethan Miller/Getty Images)