Choosing a simple, classic design like a double rider or A2-style bomber will ensure that it never really goes out of style and works with more items in your wardrobe. Avoid heavy embellishments, unnecessary zippers, etc. Less is more! And to make sure your investment is long-lived, be aware of the material- lambskin, for example, may be soft and supple but is nowhere near as tough as cowhide or goat! Balance it out: Leather jackets have an undeniably macho character, which can be tricky to work with. Keep your cool with some “softer” pieces to go with them- scarves and beanies work great in the winter, while more fitted pants and low-profile shoes do a good job of not fighting your top end. Boots, wider pants, collared shirts, and anything formal should probably be avoided. The whole idea here is to offset the “statement” of your jacket- let it take the lead, and keep the rest of your outfit relatively muted, casual. Know your history: It helps when building your look to know the origins of your jacket’s design- where it came from. The purpose a style was designed for and who adopted it can give you great clues about what you might want to try. Bomber jackets are classic Americana, and contrast well with more modern pieces like skate shoes and joggers. Moto jackets have a ton of European rock and roll history, and go great with slim jeans and oversized, draped tees. A little research goes a long way! Know when not to wear one: Now that you’ve nailed down your choice you’re probably going to want to wear it everywhere- breaking it in and making it yours is half the fun with leather. But there’s plenty of times when you just plain shouldn’t. Formal and business events are an obvious no-go, pouring rain can seep in and upset leather’s delicate balance of oils, and seriously hot weather will cause serious sweating (again, leather is porous and absorbs liquid which can damage it).