where did the term penny loafer come from
Slip-on 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.[16] Either way, the name penny loafer came to be applied to this style of slip-on and has since stuck. The practice continues, especially among those who remain committed to a classic and refined but still scholarly appearance, such as lawyers.[3]