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Um, No: The Best of the Worst of 2009

Gossip Girl Leighton Meester went for a rock 'n' roll look at the grand opening of American Eagle Outfitters (where she also performed). Unfortunately, she went a little overboard. We can see how each of the elements involved do seem very "rock star": the heavy eye makeup, the leathery dress, the bared skin. However, all of these elements in conjuction just make a girl look straight-up crazy.

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Replay Slideshow

Um, No: The Best of the Worst of 2009

Since we've been covering the style set's (often egregious) fashion missteps, there's been bad -- Mischa Barton's "Spiderwoman" dress -- and then worse -- Leigh Lezark's carnival clown suit. Here are our top 20 most memorable fashion flubs.

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