Why are they called penny loafers?

The classic shoes are called penny loafers due to how people styled them when they first emerged during the early 20th century. Young people often stashed pennies in the instep cutouts of the shoes. Initially, this was likely done out of necessity. By placing a couple of coins here, an adolescent or young adult could have some change on hand if they needed to make a call on a payphone. Eventually, slipping in the coins became a style trend that inspired the name of the footwear style. On 1stDibs, shop a collection of penny loafers.