Coin Star

The penny loafer, a long-time American classic, may conjure a mixed bag of celluloid memories. James Dean, The Paper Chase, Michael Jackson, an irrational fear of preppy, thirtysometing whiners—for better or worse, the penny loafer has undergone a perennial rise and fall in our collective style consciousness. But as a few under-the-radar shoe designers are showing, this casual but sophisticated slip-on may be the next step toward joining a more sensible men's style renaissance that's well underway.

Bridging the gap between the staple sneaker and the over-buffed wing tip, labels like Reform Party (founded by designer Kristen Lee) have hardly reinvented the wheel—though they did get it rolling again. Styles are familiar, but inspired with more modern materials, like Reform Party's cotton canvas Rustic collection available in black, fatigue, or khaki. Looking for something a little sleeker? Try Acne's Jans loafers, a structured leather option in safe shades of brown and black. Whatever style suits, rest assured there's never been a better time to save your pennies.

A fall shoe that's worth every penny.