Worst Oscars dresses of all time

A frequent inclusion to many worst-dressed lists, Cher's outlandish Oscars outfits signalled a time when celebrities still took risks on the red carpet. Marc Biggins/Liaison

It’s hard to believe, but there was a time when the Oscars were just another awards show Hollywood players were obligated to attend. There was no red carpet, no five-hour prep time with a full glam squad, and no talk-show hosts barking “who are you wearing?” into celebs’ faces.

Today, of course, it’s an entirely different game. The women are impeccably groomed (right down to their nail art), and their gowns are scrutinized from every angle before hitting the red carpet to make sure there isn’t one thread out of place or fashion faux pas that could land them on a worst-dressed list. In short, it’s boring.

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“The Oscars are almost too safe,” Nicole Ferreira, a celebrity stylist who has worked with Octavia Spencer and Elizabeth Banks, admits to Yahoo Style. “We can blame stylists for that. Stylists are afraid to take those risks because of the risk of being made fun of.”

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With just a couple of days to go until the 89th Academy Awards, we’re looking back at the glory days of the red carpet, when stylists were a mere concept and stars weren’t afraid to colour outside the lines.

Cher, 1986

It’s doubtful there has been anyone in the history of red-carpet style to make such bold sartorial choices as Cher. Bob Mackie, her longtime collaborator, starting designing costumes for her during The Sonny & Cher Comedy Hour years, and worked with her until 2014. Mackie once said of Cher: “It’s not like dressing a regular person; it’s like dressing a crazy goddess.” And her awards-show style couldn’t be more true to those words.

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Demi Moore, 1989

This was a personal effort for Moore who designed the strange bustier-and-biker-shorts ensemble. The overarching reaction from the press was: next time, let a professional do the designing.

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Jim Smeal/WireImage

Kim Basinger, 1990

Much like Moore the year before, Kim Basinger was the architect of her own look. Part princess gown and part structured blazer, some speculated that it was a nod to the gender-bending style of musician Prince, with whom she was involved at the time. “Prince is all half-and-half, though; male/female, Gemini — and I’m sure Kim thought it was a really great representation,” said Helen Hiatt, Prince’s costume supervisor of the era.

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Geena Davis, 1992

This dress, designed by costumers Ruth Meyers and Bill Hargate, perfectly encapsulated the mixed-up nature of early ’90s fashion. Considering it was the year that Davis was nominated for her role in Thelma and Louise, it could be a nod to her freewheeling character. Or maybe she was just having a laugh.

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Miranda Shen/Fotos International/Getty Images

Kate Hudson, 2001

Hudson has reportedly “forgiven” Stella McCartney for landing her on the worst-dressed list in 2001. “I blame the hair,” the designer said in an interview with Hudson at the 2012 Vogue festival. “I know it sounds like I’m trying to … but really. And the cape. I take responsibility for the cape.”

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Bjork, 2001

You might as well consider this dress the precursor to the meme, because hilarious interpretations of this design still pop up to this day. Of course, no one was surprised to see the elfin Icelandic singer in this wacky concoction courtesy of Macedonian designer Marjan Pejoski. But they were amused when Bjork playfully dropped her egg-shaped purse from the flounces of her skirt as if she was laying an egg.

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Sally Kirkland, 2002

There are so many things wrong with this look it’s hard to focus on just one. Although, the rhinestone bindi may be the worst.

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Gwyneth Paltrow, 2002

Even Paltrow, who rarely takes a fashion misstep, admitted this Alexander McQueen look didn’t work. In an interview posted on her GOOP website, she said: “There were a few issues; I still love the dress itself but I should have worn a bra and I should have just had simple beachy hair and less makeup. Then, it would have worked as I wanted it to — a little bit of punk at the Oscars.”

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Uma Thurman, 2004

The fashion media had a field day with this Christian Lacroix ensemble, to which they drew comparisons to “Swiss Miss” and “Heidi.” Thurman later said to InStyle: “It was a beautiful dress. Turns out, I wore it wrong.”

Frazer Harrison / Staff

Sophia Loren, 2009

“Madame Tussaud’s people just called: they want back Amy Adams’ dress from Enchanted,” Deadline quipped at the time. This Giorgio Armani-designed dress was altogether too much, from the bedazzled bra straps to the overzealous flounces and crystal-studded sleeves. But then again, Sophia Loren has never been known for her subtlety.

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