16. Johnny Depp
As this list illustrates, the best shortcut to a life of dressing like a street urchin is to be an actor who works with Tim Burton. Depp is no exception. We chose this from the various and sundry of Depp's hobo-inspired outfits in honor of the one-year anniversary of the Occupy Wall Street movement. In this outfit, Depp would fit right in squatting in a foreclosed home, staging a bank sit-in, or falling victim to police brutality.