Photo Credit: tresbienshop.net

In 1934, G.H. Bass started making “weejuns”, a name given to his version of Norwegian moccasins.   (With a name like Weejuns, it’s not surprising that the trend was slow to catch on).  1950’s American prep school students brought the term “penny loafer” into existence by placing a penny into the diamond shaped cut-outs of their Weejuns, popularizing the shoe. 

According to Hoyle, penny loafers are good, but pennies should remain in your pocket.

Fact credit: wikipedia