Our top pick, the Allen Edmonds Randolph Penny Loafer, is a classic shoe that can be worn with both suits and jeans. If you want to go all in on comfort, we like Amberjack’s The Loafer ...

Roberto Castro advanced to a playoff Sunday at the Wells Fargo Championship, but as it turned out, he was anything but a shoe-in to win. His approach shot on the first playoff hole actually ...

And while you won't have any trouble copping a very solid classic leather penny loafer for less than $200 (see G.H. Bass), there aren't many classic leather slip-ons for less than $100.

Unlike the previous slip-on model, both brands have leaned further into the penny loafer silhouette. The original Jack Purcell’s are a comfortable departure from the classic All-Star Converse.