Emerica Wino Mid Shoe - Men's - $32.97

Yes, Emerica makes skate shoes, but the Men's Wino-Mid Shoes look so dang good (in leather or canvas) that we suggest you save 'em for a night out and a morning after. Of course, if you pass out behind a dumpster, then you should expect the local cart-pusher to be sporting these classy skate-inspired street-kicks the next day. At that point, you deserve to stroll home barefoot, order another pair, and give said wino a high five to let him know that you appreciate is taste in shoes. - $32.97