Posted on July 16th, 2009 by Erika

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10. Bjork – Swan Dress at the 2001 Academy Awards

Bjork Swan Dress

Bjork has made her career on being…let’s just say “different”. At the 2001 Oscars, Bjork donned an absurd “swan dress” (complete with beak), to the shock and awe of celebrities and onlookers alike. So was this dress a fashion distaster? Are Bjork’s chart-toppers a musical disaster? We’ll leave the judgment to you.

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9. Chyna – Barbarian Dress at the 1999 Emmy Awards

Chyna Barbarian Dress

At the pinnacle of her pro-wrestling popularity, Jodi Laurer (aka Chyna) appeared at the 1999 Emmy Awards in what appeared to be a costume left over from Conan the Barbarian. The resulting photos are downright scary.

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8. Celine Dion – Backwards Tuxedo at the 1999 Academy Awards

Celine Dion Reverse Tuxedo

In the above photo, Celine seems to be signaling her blindness, which would account for this John Galliano reverse-tuxedo. We realize this isn’t a dress, but the outfit was too shocking to omit (and not bad enough for our Worst Outfits in Red Carpet History) list.

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7. Lara Flynn Boyle – Tutu at the 2003 Golden Globe Awards

Lara Flynn Boyle TuTu

Wearing a tutu is shocking enough, but the gaunt and unhealthy looking Lara Flynn Boyle made a spectacle at the 2003 Golden Globes red carpet.

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6. Sheryl Crow – What-the-Hell-Happened-Fashion at the 2002 Grammy Awards

Sheryl Crow Bizarre Outfit

Sheryl Crow has become a dazzling red carpet mainstay, alas, it wasn’t always this way. In 2002, Crow was spotted in a weird denim cape with stripper boots (again, not a dress, but too good to leave out).

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5. Lizzy Gardiner – AMEX Gold Card Dress at the 1994 Academy Awards

Lizzy Gardiner Gold Card Dress

1994 was a good year for Lizzy Gardiner. Not only did she take home an Oscar for best costume design, but her self-designed American Express Gold Card dress would later fetch $12,650 for charity.

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4. Trey Parker/Matt Stone – Man-Dresses at the 2000 Academy Awards

Trey Parker and Matt Stone dresses

You may look at this photo and ask “why?” The answer: Lysergic acid diethylamide. In 2006, Parker and Stone admitted to dropping acid prior to the awards show (for which they held a nomination!).

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3. Toni Braxton – Sexy White Dress at the 2001 Grammy Awards

Toni Braxton Sexy White Dress

For many, the revealing white dress that Toni Braxton wore to the 2001 Grammy’s would have been a major faux-pas. Yet the R&B soul singer was able to pull off the wardrobe-malfunction-waiting-to-happen and find her way onto many best-dressed lists.

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2. Rose McGowan – See Through Dress at the 1998 Video Music Awards

Rose Mcgowan See Through Dress

Rose McGowan’s 1998 VMA dress will forever live in infamy (and forever will be searched in Google images). The netted and strapped dress completely revealed McGowan’s breasts and backside. Marilyn Manson, her boyfriend at the time, seemed to approve.

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1. Cher – Bride of Frankenstein Dress at the 1986 Academy Awards

Cher 1986 Oscar Dress

Don Ameche’s look in says it all. Wow…

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  1. The Best Red Carpet Dresses of 2009 – Midterm Report | Red Carpet Dress Says:

    [...] has been a pretty good year for red carpet fashion. Actually, it has been a pretty tame year (no shocking dresses or wardrobe malfunctions). But tame doesn’t necessarily mean [...]

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