Fashion critics can be merciless when it comes to the Academy Awards, the most important event in Hollywood every year, but sometimes stars really make it easy for them. Huge fashion risks don’t belong on the red carpet, since they too often become fashion disasters.
See the most outrageous Oscar dresses of all time, dresses that really stood out on the red carpet, but not in the way the celebrities who wore them intended to.
Diablo Cody, 2020
Screenwriter and former exotic dancer Diablo Cody really stunned the fashion critics in 2020 with her daring leopard print dress. The Christian Dior creation might not be out of place in a resort collection, but it proved to be the wrong choice for the Academy Awards. Even if she made the worst dressed list that year, Cody went home with an Oscar for her original screenplay (“Juno”).
Barbra Streisand, 1969
Going for dressy pajamas proved to be the wrong choice for Barbra Streisand, especially since the outfit turned out to be see-through. The Scaasi sequined outfit proved to be one of the most outrageous Oscar dresses, but Streisand, whi won a Best Actress Oscar that night, later claimed that she couldn’t tell just how sheer her outfit was in the dressing room.
Vera Farmiga, 2020
The ruffled asymmetrical gown Vera Farmiga wore at the 2020 Oscars was designed by Marchesa, usually a red carpet winner. Some fashion critics praised it, but the fuchsia gown had so many ruffles that it turned out looking like a pressed flower. Farmiga was savvy enough to pair it with subtle makeup and a sophisticated updo, but the dress still stood out like a sore thumb on the red carpet.
Jada Pinkett Smith, 1997
Easily one of the most outrageous Oscar outfits, Jada Pinkett Smith’s look for the 1997 Oscars focused too little on her style and way too much on her abs. The Versace separates in mesh metal were certainly attention grabbing, but the belly chain really pushed this look over the top, in the worst way possible.
Cher, 1988
Bob Mackie has dressed Cher for most of her Academy Awards appearances and never once did the singer make the best dressed list. Her 1988 outfit was certainly one of the most outrageous Oscar dresses, as the sheer gown would have been extremenly revealing, even with the sparkly beading that barely covered her.
Charlize Theron, 2020
Another controversial choice, Charlize Theron’s Dior gown worn at the 2020 Academy Awards might have gone unnoticed by fashion critics if it wasn’t for the risky decorations on the bodice. Looking like design pasties worn on the outside of the dress, the dress looked like it was missing some tassels to complete the daring look.
Lizzy Gardiner, 1995
Made from 254 American Express gold cards, Lizzy Gardiner created and wore one of the most outrageous Oscar dresses of all time. The Australian costume designer picked up the Best Costume Designer award for “The Adventures of Priscilla, Queen of the Desert”, and her red carpet look certainly matched the over the top sensibility of the movie.
Hilary Swank, 2020
Draping tulle on top of a mini dress isn’t exactly the best way to create a winning Oscar dress, but Hillary Swank loved the Dior design enough to wear it on the red carpet. Swank didn’t impress fashion critics and ended up on quite a few worst dressed lists, thank to her ballerina-inspired dress with a matching bag.
Björk, 2020
“Laying” eggs on the red carpet might be performance art, but it’s certainly no way to gain points for fashion at the Academy Awards. Björk’s 2020 swan dress designed by Marjan Pejoski is certainly one of the most outrageous Oscar dresses of all time, but it also represents a sense of fun that’s often missing on the red carpet in Hollywood, where most people take themselves very seriously.
Helen Hunt, 2020
Breaking the rules doesn’t usually win any accolades at the Academy Awards, and Helen Hunt did it twice in the same ensemble. The navy blue creation is one of the most outrageous Oscar dresses both because it’s from H&M and because it looks in dire need of a little ironing.
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