Oscars’ Worst Dressed of All Time!

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Demi Moore

Back in 1989, the actress designed her own look, which included bicycle shorts, a bustier top and metallic-lined skirt. Needless to say, she stuck to her day job after that catastrophe.

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Kim Basinger

It's been over two decades since Basinger arrived at the 1990 Oscars in a white satin gown with a giant skirt that she designed herself, yet we're still baffled by the bizarre menswear-meets-Cinderella number.  

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Geena Davis

She was nominated for her memorable role in Thelma & Louise in 1992, but the only thing the leggy actress won that year was a spot on the worst-dressed list.

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Whoopi Goldberg

Surprise! Under Whoopi's ugly lime green-lined purple satin skirt was an even more hideous pair of pants in 1993. And who could miss the matching shoes?  

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Celine Dion

It's bad enough that the singer wore a baggy white suit in 1999, but the backwards jacket, matching fedora and sunglasses made the ensemble that much worse.

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Angelina Jolie

Jolie has come a long way from her goth days! The actress picked up her Best Supporting Actress Oscar in 2000 for Girl, Interrupted in a long black dress and inky extensions, which made her appear as though she was channeling Morticia from The Addams Family.

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Tyra Banks

The supermodel must have mixed up the date of the 2000 Oscars with the prom. How else would you explain this lavender tulle creation?

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Kate Hudson

The star's Stella McCartney gown, which featured a beaded fringe capelet, was slammed by fashion critics in 2001. But lit was really Hudson's frizzy updo that earned her a spot on the worst dressed list.  

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Bjork

Perhaps the most famous bad dress in Oscar history, the singer's 2001 look featured a fake swan wrapped around her neck and a flesh-colored bodysuit with sparkly tights.

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Gwyneth Paltrow

A year after wearing a sugary-sweet pink gown, the actress arrived at the 2002 show in an unflattering goth-inspired design.

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Faith Hill

The country singer performed "Somewhere Over the Rainbow" at the 2002 Oscars, which is exactly where she found her pastel gown.

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Hilary Swank

The actress' 2003 pink mini with hot pink tulle overlay is every preteen girls' fantasy dress.

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Scarlett Johansson

Right color, wrong fit. Johansson celebrated her 2004 nomination—for Girl With a Pearl Earring—in a pleated Alberta Ferretti creation dipped in a gorgeous teal hue. One problem: The cut of the gown didn't flatter the actress' famous hourglass shape.

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Uma Thurman

It's hard to imagine this high-fashion star looking anything but chic. However, in 2004 the presenter channeled the Swiss storybook character Heidi in a white dress with poufy sleeves.

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Diane Keaton

Usually we respect Keaton's quirky style, but the menswear look she wore in 2004, which had a vest, tie, hat and gloves, was more like a costume than a red carpet outfit.

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Jessica Biel

It wasn't so much the weird folds of fabric on her white strapless dress that made it so bad in 2009. It's the fact that Biel paid a stylist to pick out the underwhelming look for her.

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Charlize Theron

While it doesn't come close to some of the awful looks on this list, the strategically placed rosettes on Theron's Dior Haute Couture design made it a fashion fail at the 2010 awards.

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Anne Hathaway

When she picked up her Oscar in 2013, Hathaway certainly seemed uncomfortable in her pink Prada dress with awkward darting—and that's because it wasn't her first choice. As Hathaway explained to Harper's Bazaar, she had already chosen her dress by Valentino. But when her Les Miserables costar, Amanda Seyfried, revealed her Oscars dress—nearly identical, save for the color—Hathaway felt that she needed a new look. Enter the pretty, but not quite perfectly tailored, Prada.