Pilot suede bomber, $212 by Obey

Popularized by military pilots in the 1950s and given the Army-Navy specification number MA-1, the nylon waist-length bomber jacket was a jet-age replacement for the heavier shearling-lined flight jacket. Today's versions are a little more modern, but just as macho. The military details have been toned down a bit, the material softened and the silhouette has slimmed down—the result has become the style set's go-to outerwear for 2016. And why not? The jacket makes a cooler sub-in for your blazer and is an ideal layering option when the temperature drops.