The word "preppy" was originally used to describe someone who attended a private college-preparatory high school (called a "prep" school). Gradually, the term came to mean any young person who was upper class and snobbish, and also described the style of clothes such people wore. The word was widely used in the 1980s as a negative term describing the superficial values of those with a privileged lifestyle. By 2000, it was mostly found in articles about fashion. Its meaning had become less negative, simply describing the button-down collars and loafers that are considered the preppy style.

Though the word "preppy" had been used on the East Coast for many years, it was widely popularized by two books published a decade apart. Love Story, a novel published in 1970 by Erich Segal (1937–), tells about the romance between two college students, one an Italian American working-class woman and the other an upper-class...