If you thought Anna Wintour was one of those women who slept in a Prada dress, take note: the Vogue editor-in-chief does go casual. She donned a pair of J.Brand $158 skinny jeans with a Proenza tee for a match at the Sony Ericsson Open. Later, she changed into a more "Anna" outfit, sporting Prada's Spring banana skirt and a white crochet sweater, with nary a hair out of place. While we're all for the banana skirt, we have to say, Anna-in-jeans is a refreshing sight. What do you think?