There is probably not a single model of shoes I wear more frequently than the penny loafers. The model originated from a creation by the bootmaker G.H Bass in Maine during the mid-thirties and was originally called Weejuns due to the history of Norwegian farmers wearing a similar style of slip-ons. What made the Weejuns unique was the strap over the upper which featured a diamond style cut-out. This was purely a design feature but came in handy years later when the name “penny loafer” was coined (no pun intended).
Many seem to believe that the phrase “Penny loafer” came from the idea that the diamond cut-out was designed to house two penny´s for an emergency phone call from a pay phone but this theory has been proven to be an urban legend due to the fact that the American pay phones never accepted pennies. A more accepted story was that American students in the Ivy League universities during the 1950s made a fashion statement by placing a penny in the same space.
From being a strictly casual footwear, the model quickly saw a rise in popularity in more formal situations and was frequently worn by style icons such as Clark Gable and Cary Grant. It became almost a key feature in the Wall Street uniform during the 1980´s and a version in black calf is still considered appropriate for business in many cultures such as the US and Japan.
One of the things I´ve always loved about the penny loafer is its versatility. In black calf it is a wonderfully elegant option to a dark worsted suit but the same model in a mid-brown suede works equally well with your favorite pair of jeans. Many might consider the penny loafer, strictly as a summer option but I highly recommend it with heavy mid-grey flannel trousers and matching socks during autumn and even winter. With our Scandinavian climate being quite harsh during the coldest months, I would prefer a version with a thin rubber sole, either from the manufacturer or added later by your local cobbler. This will protect and isolate your feet from moist in a superior way compared to a bare leather sole on the rainy or snowy Stockholm streets.
There are many different styles of penny loafers. Some prefer the neat Italian versions with a Bologna or Moccasin construction to make the shoe as soft and flexible as possible. I prefer the more traditional British tradition with a goodyear welted construction, easy to refurbish down the line and with a traditional classic round last and a slightly shorter vamp.
Andreas Weinås is Style Editor at King Magazine, co-founder of the podcast Gentlemanualen and a style and watch enthusiast. What sets Andreas apart from most other aficionados is his deep knowledge and experience in style and watches. His curiosity to learn about what’s actually behind production, materials and quality can almost be compared to an obsession. Andreas is a guest editor on Morjas Blog where he shares his experience and thoughts around style, life and history.