The penny loafer is quite literally a remnant of a bygone era – a time when pay phones were a vital part of daily life and a penny could be a lifesaver. Although, when Bass first debuted the shoe in 1936 the name that they gave to it had nothing to do with currency. As a reference to Norwegian farmers who were the first people seen wearing loafers in a 1930 Esquire article, Bass called the shoe, “The Weejun.” Companies had already been making flat front loafers for several years, but John Bass wanted to add something unique to his shoes. Bass decided to put a small strap across the top of the shoe, but it was the signature lip shaped cutout in the center of strap that made the Weejuns a classic.
Initially it was just a nice little detail to differentiate a Weejun from all other loafers, but after a few years the opening became a practical pocket. In the 40′s and 50′s a phone call cost about a penny, and so Weejun wearers began slipping pennies into the front of their loafers as a backup in case they ever needed to make an emergency call. Eventually, the pennies just stuck, and even after phone rates had been raised people were still putting pennies in the cutout of their Weejuns. In the 60′s the sockless look became popular as preps began pairing their penny loafers with everything from shorts to sack suits. This high/low versatility has helped the penny loafer endure for decades as a simple spring staple.