An outerwear piece is a serious decision. You’ll wear it over everything, you’ll be photographed in it constantly, and if you get it wrong it will undermine every good outfit underneath. We’ve put real thought into this section because the stakes are higher here than almost anywhere else. Structured coats that earn the investment, leather jackets worth the splurge, lighter options that actually work for the transitional months when the weather refuses to commit. These are the pieces that go over everything and make everything look better.