Penny loafers are a preppy classic and one of the best options for hot weather and casual wear. But how much do you really know about this classic style of Italian leather shoe?

People trace the history of penny loafers to the 1930s when a couple different companies started offering loafer styles. In 1936, shoemaker G.H. Bass introduced his Weejun style; many people consider this the ‘first’ loafer. Another account references shoes the Spaulding company produced after an article in Esquire covering dairy farmers Norway showed off an easy-to-wear slip-on shoe native to the area. Requiring only one large piece of leather to wrap around cradle the foot, it was an easy style to construct with a modest use of quality material. Whatever the origin, the loafer soon became a hit in America with its hand-sewn moccasin construction and casual look.

Of course, its simple design didn’t designate it to casual style only. The comfort and ease of the loafer lent a sense of balance to more formal wear and soon men were wearing the loafer with their suits. Of course, men wore a lot more suits back then… but that’s a topic of discussion for another day.

So where does the ‘penny’ in penny loafer come from? The popularity of the Bass Weejun and its signature leather strap with an eye-shaped slit caused many imitations. The strap soon became standard for the loafer style, adding a bit more detail to an otherwise plain leather shoe. Without laces or buckles, the simplicity of the style necessitated something that added interest without turning it into something it wasn’t. This style of loafer became very popular amongst young men—specifically the prep school and college crowd. So the story goes that the kids began fitting pennies beneath these leather straps. The perfect hiding spot for a little pay phone change in the age before cellular.

However much the times have changed, the popularity of the penny loafer has stayed steady—grown even! Mostly worn without socks since the 1960s, men continued to wear their penny loafers with all styles of dress. They were a staple of the 1980s prep style movement and continue to be a popular choice amongst style icons and celebrities. Not only have they proven versatile enough to go between casual and formal, but they’ve crossed the gender line as well. Penny loafers prove to look just as good on the ladies as they do on you, gents.

With such long lasting popularity and a storied history, the penny loafer makes a great addition in every man’s shoe wardrobe. If you haven’t invested in your perfect pair of pennies yet, may we suggest the Stewart Penny Loafer? We offer it in seven different colors and finishes, all of them worthy of a spot in your closet. Check them out here.