What could be more glamorous than dressing like a homeless person? For some in Hollywood, the answer is not much. We have waded into the barren wasteland of “Worst Dressed Lists” to find the greatest of the Hollywood vagabonds. While some of them are doing this for fashion, some do it because they are weird, and some are doing it because they are so high they don’t know what they are wearing. Every one of these celebrities is dressed like they are homeless. Think about that. Tie your bindle to a stick and jump the next freight: we present to you the gallery of Celebrities Dressed Like Homeless People.