The Oscars have always been one of the biggest fashion nights of the year, with many red carpet looks remaining in the cultural lexicon since the annual awards show started nearly a century ago.
Many of the best Oscars red carpet dresses were worn by actresses who went on to pick up their own awards in a moment that merged their achievement with a standout fashion moment. This has been seen many times over the decades, including in 2002 when Halle Berry became the first Black woman to win an Oscar for Best Actress for her role in “Monster’s Ball.” The actress celebrated her landmark win in an Elie Saab dress that consisted of a mesh floral print top with a draped silk burgundy skirt, which has become one the Oscars’ best dresses of all time.
Gwyneth Paltrow had a similar moment in 1999 when she won the Oscar for Best Actress for her role “Shakespeare in Love,” where she accepted her award wearing a light pink, spaghetti strap Ralph Lauren dress that was reminiscent of the old Hollywood glamour dresses worn by the likes of Grace Kelly.
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Vintage looks have also reigned as some of the best Oscars dresses over the years. For instance in 2006 when Reese Witherspoon won the Oscar for Best Actress for her role in “Walk the Line.” The actress wore a champagne-hued beaded Dior dress from 1957, which she explained in a 2020 Twitter thread is one of her favorite red carpet dresses she’s ever worn.
While many actresses in recent years go with an old Hollywood glamour look for the Oscars, that style was first popularized by the stars of the 1950s and 1960s at the awards show, such as Audrey Hepburn in a floral print Givenchy gown in 1954 and Grace Kelly in a silk Edith Head gown in 1955.
Many of the Oscars’ best dresses of all time have received that title for their couture-like qualities, while others have earned it by being controversial. Take musician Björk’s swan-themed Marjan Pejoski dress. The dress may have had a polarizing reaction among Oscars spectators, but it is still one of the most memorable looks on the red carpet.
Here, WWD rounds up some of the best Oscars red carpet dresses of all time. Click through the above gallery to see more.
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