2008, Hillary Clinton, Letterman

Get a leg up No, Hillary Clinton is not trying to hail a cab. She's waving to fans outside David Letterman's TV show in New York in Feb of this year. But notice that she's also wearing a slightly higher heel, which she should definitely do more often. It makes her legs look longer and every woman on the planet needs that. Related: Cindy McCain: Politics of fashion Michelle Obama: Politics of fashion Sarah Palin: Politics of fashion
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