Old Familiar Memories - Photo 164

Penny Loafers

A bespoke shoe company based in London that was established in 1847 developed the first loafer as a country house shoe for the landed gentry and the royal family. The "Wildsmith Loafer" made by Raymond Lewis Wildsmith of Wildsmith Shoes, was designed for King George VI as a casual house shoe.

The term penny loafer has uncertain beginnings. One explanation is when American prep school students in the 1950s, wishing to make a fashion statement, took to inserting a penny into the diamond-shaped slit on their Weejuns. Another theory is that two pennies could be slipped into the slit, enough money to make an emergency phone call in the 1930s.