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.
Penny loafers are a laceless shoe, or slip on, with a moccasin-style upper attached to a sole and heel. Its defining feature is a strip of leather that sits across the instep, commonly known as a “saddle,” with a small cut-out just large enough to place a "penny".
By the 1940s the penny loafer had gained popular culture status. "Prep style" was in and Ivy League students embraced the penny loafer as an essential part of this look. Soon America’s most powerful men, including President John F. Kennedy, were wearing them. Owning a pair of Penny Loafers suddenly became de rigueur in American culture - in much the same way that Chelsea boots have become in Australia.
From left to right: The original North American Makasin. The Norwegian Moccasin circa 1908. The G.H. Bass 'Weeguns' circa 1934.
Australian Men & Penny Loafers
To be fair, Aussie men have not flocked to own Penny Loafers. While it's a popular shoe with the stylish class, many Aussie men may feel it's a bit too 'fancy' for the average cobber. However, the truth is that the Penny Loafer is one of the most versatile shoes a man can own; especially now, where dress codes are becoming increasingly blurred and people seek greater flexibility in how they dress. Furthermore, it's essentially a shoe version of the much-loved Chelsea Boot. Infact, we'd go so far as to say that the Penny Loafer is to the Urban sprawl as the Chelsea Boot is to country life. A shoe with such utilitarian value means one doesn't need to dress like a Pitti Peacock to enjoy them.