Posted on July 16th, 2009 by Erika

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With every passing red carpet event, there are dozens (if not hundreds) of best and worst dressed lists. Yet pop culture has a fleeting memory – both great and horrible outfits are often forgotten only days after an event. But what about the true fashion bombs that certain celebrities have dropped on us over the years? Surely, they deserve a more permanent home.

Presenting the 10 Worst Dressed Celebrities in Red Carpet History:

10. Bette Midler at the 1975 Grammy Awards

Bette Midler - 1975 Grammy Awards

Beginning our list is an oldie-but-goodie. Better Midler arrived to the 1975 Grammy Awards in a sequined dress with a 45 in her hair (perhaps Lady Gaga found her button hat inspiration here). Stevie Wonder’s blue tux isn’t so flattering either, but give the guy a break, he’s blind.

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9. Macy Gray at the 2001 Grammy Awards

Macy Gray - 2001 Grammy Awards

There’s nothing wrong with a little self promotion, but Macy Gray’s 2001 Grammy dress crossed the line. Maybe it was the industrial fasteners holding the seams, maybe it was the deflated soccer ball on her head…whatever it was, it didn’t work.

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8. Diane Keaton at the 2004 Academy Awards

Diane Keaton - 2004 Academy Awards

Trying to rekindle the androgynous look that brought her fame in 1977’s Annie Hall, Diane Keaton came off looking like Charlie Chaplin at the 2004 Academy Awards.

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7. Mary Kate Olsen at the 2007 7th on Sale Gala

Mary Kate Olsen

This dress is a mess. The boxiness of the garment (not to mention the fact that it looks like a window dressing) make this Olsen twin look 4-foot tall and bow-legged.

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6. Cyndi Lauper at the 1984 Grammy Awards

Cyndi Lauper - 1984 Grammy Awards

If anyone but Cyndi Lauper was caught wearing this nightmarish Pee-Wees-Playhouse-esque outfit, they may have topped our list. But hey, it’s Cyndi Lauper.

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5. Mel B at the 2008 MOBO Awards

Mel B - Scary Spice

Scary Spice looks absolutely frightening in this horrific hooded vampire dress. Yikes! (Perhaps she should have added some Twilight-esque sexy vampire makeup.)

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4. Lil’ Kim at the 2004 MTV Video Music Awards

Lil Kim - 2004 VMA Awards

Lil’ Kim has worn some controversial (read: terrible) dresses in her day, so this was a tossup. We’re going with this unflattering dress worn to the 2004 VMAs, simply because she was in no shape to wear it. At least she didn’t have a red carpet wardrobe malfunction.

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3. Steve-O at the 2006 Jackass: Number 2 Premiere

Steve O - Pees on Red Carpet

What a jackass! Not only did Steve-O sully the respectability of red carpet tradition by arriving to his film premiere looking like a homeless man – he had the audacity to urinate on the red carpet. For shame!

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2. Imogen Heap at the 2007 Grammy Awards

Imogen Heap - 2007 Grammy Awards

At the 2007 Grammy Awards, Imogen Heap arrived in a mish-mosh of an outfit that looks like something Annie Lennox would have worn twenty years prior – and that is not a good thing.

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1. M.I.A at the 2009 Grammy Awards

MIA - 2009 Grammy Awards

M.I.A’s past fashion choices have always been questionable (remember the sheer body suit exposing her third trimester baby bump). Alas, the frock that she wore to the 2009 Grammy Awards takes the cake and tops our list. Please feel free to share any other fashion disasters in the comments section.

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