The iconic penny loafer. Pigeonholed as a casual shoe, yet worn by Presidents; considered antiquated by some, yet favoured by fashionable society. It is little wonder that most men are a bit unsure about the penny loafer. The truth is, it is an extremely convenient, comfortable, and versatile slip-on shoe. This guide is designed to cut through the noise and help you get to know, and indeed how to wear, the understated Penny Loafer.