Anna Wintour

Obviously, when it comes to nailing the look of everyone's favorite fashion editrix, it's all about the hair. A perfectly sleek brown bob wig would be perfection, but if you're in a crunch, a faux bob YouTube tutorial is the next best thing. Deck out in a blazer, Chanel-style tweed, and, of course, some giant sunnies. Carry around the latest copy of Vogue and demand a cup of coffee from everyone you meet.
[Photo via @jessicadeanmoore]