For men, preppy fashion has its roots in the Ivy League style of dress, which started around 1912 and became more established in the late 1950s. J. Press represented the quintessential Ivy League style, stemming from the collegiate traditions of Ivy League schools. In the mid-twentieth century J. Press and Brooks Brothers both had stores on Ivy League school campuses, including Harvard, Princeton, and Yale. Preppy fashion emerged in the late 1970s with cues from the original Ivy League style. Some typical preppy styles also reflect traditional upper-class leisure activities, once associated with the wealthy English who once had a strong political and social position in the Northeast and New England, such as polo, sailing, hunting, fencing, crew rowing, lacrosse, golf, tennis, rugby, squash and swimming. This association with old English inspired outdoor activities can be seen in preppy fashion, through stripes and colors, equestrian clothing, plaid shirts, field jackets, and nautical-themed accessories. By the 1980s, mass marketing of brands such as Lacoste, Daniel Cremieux, Izod, and Dooney & Bourke became associated with preppy style in many areas of the US and Canada.
For women, preppy-influenced fashions emerged in the 1960s, a trend led by designers such as Perry Ellis and Lilly Pulitzer, influenced by designers such as Oleg Cassini, and popularized by female students at the Seven Sisters Colleges, sister institutions to the Ivy League. These classic ensembles of the 1960s and 1970s 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.
Though traditional interest in preppy style fell in the 1990s, some of the newer outfitters such as Ralph Lauren, J. Crew, Vineyard Vines, Gant, and Elizabeth McKay are perceived as having preppy styles, with designers such as Marc Jacobs and Luella Bartley adding the preppy style into their clothes in the 1990s.
Examples of preppy attire include argyle sweaters, crewneck sweaters, grosgrain or woven leather belts, chinos, madras, Nantucket Reds, button down Oxford cloth shirts, pearl necklaces and earrings, gold bangle or large chain bracelets, penny loafers, polo shirts (often with a popped collar), and boat shoes.