15. Bicycle

Even if it only gets ridden a few times a week, a lesiurely bicycle is a stylish item that can make you look awesome without the hipster connotations. They key is to have a nice frame in a subtle colorway with leather accents like a Brooks saddle or a basket in the back for groceries (like beer). You'll also want to have brakes, and consider single speed instead of fixed gear. If you're a hardcore cyclist, by all means have your other other ride ready for the Tour De Blood Dope, but have a trusty steed ready for things like biking to a cafe or just a simple afternoon ride in jeans and a blazer.