As styles change and trends come and go, the origins of both particular styles and the words used to describe them often get lost. Wingtips likely got their name from the wing-shaped piece of leather that is laid over the toe of the shoe. This piece of leather not only resembles a wing but also creates the letter “W” on the top of the shoe. Shoes with a straight edge rather than a “W” are not true wingtips and are known instead as cap toes.

Wingtip History

Although viewed as a classic dress shoe in modern society, the wingtip shoe of today has predecessors that trace back to Scottish and Irish peasants in the late 1700s. The soggy bogs in the region were travelled on foot quite frequently, and it was impossible to keep water out of shoes. Rather than trying to stop the water from coming in, shoemakers punched holes in the leather to more readily allow the water back out. These holes were known as “broguing;” a nod to the Gaelic word “brog,” which means “shoe.” Eventually broguing became popular with English nobility, who enjoyed shoes with decorative broguing patterns. A darkly colored leather wing was added to the front of the shoes to help prevent water from coming in quite as readily and to prevent grass stains from showing on light-colored shoes worn to sporting events. The trend came to the United States with the soldiers who returned home after World War I.