40. Maggie Gyllenhaal, 2007
Maggie Gyllenhaal is renowned for her offbeat approach to fashion: she wore turquoise leopard-print Lanvin to the 2009 Oscars. But we prefer the dark blue Proenza Schouler gown Gyllenhaal wore back in 2007, despite the unfortunate creases around her hips (satin is never anyone's friend).
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