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Worst Oscar Dresses Of All Time: A Gallery Of The Academy Awards' Biggest Fashion Flops (PHOTOS)

First Posted: 02/25/2012 9:19 am Updated: 02/25/2012 9:20 am

While there are some Academy Award dresses we've LOVED over the years, there have also been a few that we'd like to honor with a place in our hall of shame.

The bad gown can take anyone as its victim -- just look at gorgeous Gwyneth Paltrow, who made both our Best Dresses of All Time list (with her 2011 Calvin Klein)... and this more dubious rap sheet.

Check out our gallery of the worst ever Oscars gowns below! We're praying we don't have anything to add to this list come Sunday.


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  • Star Trek State Of Mind: Whoopi Goldberg

    Whoopi Goldberg dressed in full 24th century regalia at 1993's Academy Awards. (Barry King, Liaison / Getty Images)

  • Do Not Sit Behind Me: Cher

    Donning a headdress that would put Cleopatra to shame, Cher made her mark on 1986's Academy Awards. Two years later, this fashion pariah would go on to win Best Actress Oscar for her role in "Moonstruck." (Julian Wasser, Liaison / Getty Images)

  • Periwinkle Blues: Kate Hudson

    While her sheep skin coat and crop top-wearing character in Cameron Crowe's "Almost Famous" won her the nomination, Kate Hudson would not have such fashion luck during the 2001 Oscars. (Getty Images)

  • Technicolor Nightmare: Faith Hill

    Rainbow, no matter who -- even a sunny country star like Faith Hill-- or when (2002) is a mistake. It doesn't matter if the pink, yellow, green and blue brings out your eyes. No.

  • Hybrid Horror: Geena Davis

    The 1992 Oscars were full of life lessons: Sometimes you can't have your cake and eat it, too.

  • Interview With A Vampire: Demi Moore

    Just remember, 1989 was way before "True Blood."

  • Oh, Boy: Celine Dion

    Still basking in the glow of her "Titanic" ballad, Celine Dion was thought to be unstoppable. I guess that made the 1999 Oscars her Waterloo.

  • Shrink Wrap Mishap: Hilary Swank

    Hilary Swank decided to go with pink tulle for the 2003 Academy Awards. The issue here: pink tulle.

  • Is That A Backpack?: Uma Thurman

    This 2004 Christian Lacroix getup was confusing to all -- especially to Uma Thurman who later confessed, "It was a beautiful dress, turns out I wore it wrong."

  • The Color Of Couch: Jennifer Connelly

    Jennifer Connelly took home the gold for her "Beautiful Mind" performance in 2002, but unfortunately, her "meditation on beige" ensemble was far from a winner.

  • Sheer Regret: Gwyneth Paltrow

    In 2002, even fashion fave Gwyneth Paltrow couldn't make this sheer number sing.

  • Surf's Up: Sarah Jessica Parker

    Sarah Jessica Parker broke a lot of SATC hearts back in 2010 with this meringue-colored mess. It's OK! You can still want to be Carrie!

  • Sawn's The Word: Bjork

    In the years since 2001, when Bjork hit the red carpet wearing a swan costume, this outfit has made the remarkable switch from unbelievably bad to just unbelievable. Well done, Bjork!

  • Queen Frostine: Kim Basinger

    1990 was a strange time. Don't remember? Perhaps Kim Basinger dressing as the woman from Candyland during the 62nd Academy Awards will jog your memory.

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Filed by Jessica Misener  |  Report Corrections