Style: Penny Loafers

Loafers are slip-ons with a strap of leather running across the “puso” or saddle of the upper. The heart can either be machine stitched or hand stitched. Wholecut loafers can also have penny straps and can be made aesthetically accurate by creating a faux saddle using pinching methods.


The original loafers can be traced back to mid 1800s as a house shoe. It was designed so that the landed gentry at the time would have closed footwear inside the house. It was casual in nature which has since then evolved into one of the most versatile styles.

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Around 1936, American bootmaker brand G.H. Bass introduced the Weejun design. The design incorporated a strip of leather running across the saddle with a diamond shaped cut at the center. This classic became a summer house shoe but eventually evolved into a casual style staple for men and women alike. The term penny loafer came about when it is said that one could slip 2 pennies in between the slits of the strap which is enough to make emergency calls back when payphones were still a very relevant form of communication.

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It is during the mid 1950s to the 1960s where penny loafers (or loafers in general) became acceptable when paired with a suit, but only in America at the time. This would become even more acceptable as Italian shoe designers started coming up with their own iterations of the loafer design which is sleeker and dressier than their American/British counterparts.

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So even until now, the penny loafer enjoys a place in peoples’ hearts as a classic style which can be worn casually with shorts or dressed up with a suit. This style also enjoys the versatility afforded by double monks to its owners. The formality of the design though can be distinguished by the shape of the shoe last used and the height of the heel. I personally would consider lower heeled penny loafers to be more casual as it nears the level of driving loafers. I do see a lot of people wearing driving loafers (penny loafers or otherwise) with suits which is a bad pairing in my opinion. Brands like Cole Haan also released penny loafers with rubber shoe soles which is a great design idea since it adds more fun to a relaxed yet classy design.

Classic penny loafer Luna 1. On c013 last.

Overall the penny loafer is a style staple which is versatile enough to be worn with a variety of ensembles depending on the type of penny loafers. Classic bulkier loafers are the most versatile while Italian inspired dressy loafers are best worn with smart casual and business attires. Almost everyone has had a penny loafer (or a regular loafer) at least once their lives as this style appeals to both men and women with its classic chic.

Toddlers’ penny loafer.

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