Preppy fashion started around 1912 to the late 1940s and 1950s as the Ivy League style of dress. J. Press represents the quintessential preppy clothing brand, stemming from the collegiate traditions that shaped the preppy subculture. In the mid-twentieth century J. Press and Brooks Brothers, both being pioneers in preppy fashion, had stores on Ivy League school campuses, including Harvard, Princeton, and Yale.
Some typical preppy styles also reflect traditional upper class New England leisure activities, such as equestrian, sailing or yachting, hunting, fencing, rowing, lacrosse, tennis, golf, and rugby. Longtime New England outdoor outfitters, such as L.L. Bean and the recently-revived brand Madewell, became part of conventional preppy style. This can be seen in sport stripes and colours, equestrian clothing, plaid shirts, field jackets and nautical-themed accessories. Vacationing in Palm Beach, Florida, long popular with the East Coast upper class, led to the emergence of bright colour combinations in leisure wear seen in some brands such as Lilly Pulitzer. By the 1980s, other brands such as Lacoste, Izod and Dooney & Bourke became associated with preppy style.
For professional women, preppy-influenced fashions became dominant beginning in the 1960s, a trend led by designers such as Perry Ellis, and influenced by designers such as Oleg Cassini. The classic ensembles often seen worn by professional women in East Coast cities and elsewhere include tailored skirt suits, low heels, wrap dresses, shift dresses, silk or cotton blouses, and jewelry with a refined style. Such clothing often includes elements drawn from typical preppy style, such as nautical stripes, pastel colours, or equestrian details. Some "cultural icons" of preppy style for professional women include Audrey Hepburn, Grace Kelly, Jacqueline Kennedy Onassis, and 20th century New York socialites Gloria Guinness, Babe Paley, Slim Keith, and C. Z. Guest, all women whose style is often referenced by designers.
In recent years, newer outfitters such as Ralph Lauren, J. Crew, Vineyard Vines, and Elizabeth McKay are also frequently perceived as having preppy styles, with designers such as Marc Jacobs and Luella Bartley adding the preppy style into their clothes in the 1990s. New York City maintains itself as the headquarters for most preppy clothing lines, such as J. Press, Brooks Brothers, Daniel Cremieux, Ralph Lauren, and Kate Spade New York, underscoring preppy subculture as a reflection of Northeastern culture.
Examples of preppy attire include argyle sweaters, crewneck sweaters, grosgrain or woven leather belts, chinos, madras, Nantucket Reds, button down Oxford cloth shirts, seersucker cotton suiting, pearl necklaces and earrings, gold bangle or large chain bracelets, loafers, and boat shoes.