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 is an easygoing piece of outerwear. Simple enough to pull on for cool autumn days or layered up for cold, damp nights. After all, a piece that was built to keep a soldier warm in war should suffice for nights walking home from after-work drinks, son.

Shown left: $670 by Private White V.C.