A leather jacket is an investment piece every style-savvy guy should consider—and you'll never go wrong with a black biker jacket. Adding a gritty retro vibe to almost any look, this jacket can be seen on everyone from A-list actors to skate park rebels. When you buy your own make sure it's cut in a modern fit—with snug shoulders, a form-fitting midsection and sleeves that don't extend past the wrist. While there are endless ways to style this piece I like to pair mine with skinny black jeans and a crewneck sweater over a crisp white button-down. Keeping the look polished and cohesive I finish things off with a clean pair of white sneakers.