• Anatomy of a Classic: Learn more about the Bass Weejun: celebrating 75 years of shoe making.

Bass, $99

The Loafer

James Dean, Paul Newman, JFK and Michael Jackson. Men with decidedly disparate styles and yet one shoe unifies them—the loafer. Seventy-five years ago, G.H. Bass & Co. introduced the loafer to America. The design was inspired by an old Norwegian shoe, resulting in a lasting "Weejuns" nickname. The style eventually swept through America's college campuses, which is perhaps why it seems like such a fitting style for fall. Of course, they work in ankle-bearing temperatures, but there's a certain professorial charm when paired with some striped socks and some cuffed pants. The style above is the Longwood by Bass, a flat strap loafer with a hand-sewn, leather moccasin upper, cushioned leather footbed and sturdy leather soles. Other options: L.L. Bean Signature's take on the traditional beefroll style or Cole Haan's tassel loafers in antiqued burgundy leather.