The iconic penny loafer is said to have originated in the US in the 1930s. Originally the penny loafer was made to be worn indoors. They were designed with a distinctive strip of leather across the saddle with a diamond cutout.
At first Penny Loafers were called Weejuns, hailing from "Norwegians", as Penny Loafers were said to have been worn by Norwegian farmers.
Penny Loafers were made iconic by American students in the 50s when they started to insert a penny into the diamond slit, hence the name “penny loafer”. A trend was born and penny loafers are still one of the most popular loafer styles to date.