Shown: Schott NYC Leather Jacket
Buy It Now At Bloomingdale's Stores

Most things get lamer with time, but leather jackets do quite the opposite. For one, leather takes some time to fit to your body. So the longer you have it and the more you wear it, the better it'll fit you. Not to mention, the leather gets softer as it ages. A brand new leather jacket from brands like Schott NYC can cost upwards of a few hundred dollars, but the more you wear it, the more valuable to you it becomes.