Florence Welch, Miley Cyrus, Leighton Meester, Emmy Rossum, Serena Williams, MET Gala, Worst Dressed

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The higher the fashion, the harder they fall.

As the bona fide Oscars of fashion, the Met Gala red carpet is a high stakes field for the style elites. True, many stars rise to the occasion and drop jaws with their killer getups. But not everyone there is dropping jaws for the right reasons.

Among them is Madonna at the 2009 gala, whose crinkly ruched Louis Vuitton ensemble was over-the-top in more ways than one (literally). And while vintage Saint Laurent is usually a safe bet, there's no question as to why Kirsten Dunst's draped curtains-turned gown—and matching headpiece—landed on the worst dressed list at the 2007 fête.

While her Gossip Girl alter ego may have commanded the Upper East Side with her razor-sharp styles, Leighton Meester wasn't persuading anyone to join her fashion legions with that bizarre Louis Vuitton jumpsuit back in 2009. It's even more painful to see Emmy Rossum—whose style now is flawless—in that Ralph Lauren marching band uniform-turned-dress in 2006.

And Serena Williams: What's with the feathers? The tennis pro just plain missed the mark with her voluminous Oscar de la Renta design back in 2011. 

Well, folks, they can't all be Anna Wintour-worthy

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