Wing tips are men's lace-up oxford shoes that are designed with a decorative leather cap on the toe, which is cut in a "winged" design. The cap usually also has other ornamental touches, such as patterns of holes cut or pressed into the leather. First designed in the early 1900s as a high-heeled dress shoe with a wide bow, wing tips have remained as a fashionable lace-up shoe for men into the twenty-first century.
While boots had been the fashionable footwear for men at the end of the 1800s and the beginning of the 1900s, by 1910 shoes returned to favor. By the 1920s male footwear was not only functional but also quite colorful and stylish. A new "cap toe" shoe came into fashion, which had a second layer of covering at the end of the toe, partly for protection and partly for decoration. The wing tip was an elaboration on the straight cap toe design. Where the original cap had been cut straight across the toe of the shoe, the wing tip was cut into a scalloped shape, with a point in the center. The cap was then decorated with holes and designs stamped into it. Many flashy wing tips of the 1920s were two-toned, with the body of the shoe white and the cap and heel either brown or black. Two-toned wing tips were called "spectator shoes," and some fashion historians think that their design was an imitation of the popular spats, a protective cloth garment that covered the shoe from toe to heel. Sporty wing tips sometimes had a fringed flap of leather that covered the shoelaces.
Though wing tips began as part of fashionable young men's wardrobes during the Roaring Twenties, the period of time following World War I (1914–18) when Americans were experiencing a newfound freedom and sense of rebellion, they soon became one of the most popular conservative shoe styles for men, who wore them not only as dress shoes but also as part of a middle-class business uniform. Well into the 2000s wing tips have remained the preferred style of business executives, lawyers, and other male professionals. In fact wing tips are so identified with white-collar males that the shoe has come to represent the corporate world. In headlines such as "The Gumshoe Gets Wingtips: Private-Investigator Business Takes on Corporate Identity" from The Washington Post in 1997 and "Generals Trade Their Army Boots for Wingtips in Trek to Civilian Jobs" from a 1996 article in The Christian Science Monitor, it is generally understood that putting on wing tips means entering the business world.
Schoeffler, O. E., and William Gale. Esquire's Encyclopedia of 20th Century Men's Fashions. New York: McGraw-Hill, 1973.