As far as traditional footwear goes there are a lot of options out there. You can wear wingtips, plain toe bluchers, saddle shoes, bucks, moccasins and the list goes on (almost anything that does not have a square toe). However, there is no other footwear that is as quintessentially American as the penny loafer. Like most things quintessentially American it has roots somewhere else.The loafer was not invented in America, but rather in Norway. It was a casual shoe worn by dairy farmers and made by off-season fisherman. The shoe was introduced in America after World War I by the Spaulding company and popularized by Esquire Magazine.
Bass started producing their version of the loafer in 1936. Their loafer was a little different. It had an extra strip of leather across the top and a diamond cutout. It was called the Weejun. One can presume this name borrows from the word Norwegian as the penny loafer was borrowed from the culture of Norway. The loafer started out as a casual shoe and worked its way into more formal settings. It was a staple on college campuses in the 1950′s and is synonymous with Ivy League style. In fact, it was students who started the practice of placing pennies in the diamond cutout and in doing so helped create the term “penny” loafer. The penny loafer can now be worn in a variety of settings without causing a stir. Whether you are in denim with a flannel shirt or a blazer with wool trousers, penny loafers will look appropriate.
Currently, there are many companies that manufacture a very nice penny loafer. I myself am a fan of the Weejun. There is a Bass outlet not far from my home. I can purchase a pair there for somewhere between $50-$70. This is a nice markdown if you consider that the average retail price is around $100. The fact that they are affordable, available and classic are the reasons that lead me to continue to purchase Bass Weejuns. They also fit me. This last attribute cannot be overlooked. I have tried to make many pairs of shoes fit, that just will not. Due to my stubbornness, and my desire for these shoes my feet have suffered through many days, but not anymore.