5. Vans Larkin "Black Out" Perforated Black Leather, $75

"We've all been there. We've all danced with the devil in the pale moonlight and awoken in a strange bed in Bushwick with puke on our shoes. The key is how you handle it. Perforated leather is your friend. It's summer, find a fire hydrant and get in there and hose them dogs off. Inside and outside. Quick dry and you are a new man. Quick stop at the clinic and you're back at Tompkins with an iced coffee in no time."