In Dead Poets’Society, a cast of young actors showed a new generation how preppy originally looked, and reignited an interest in it. Photo courtesy Touchstone Pictures
Style Necessary Style

A short history of preppy style

Preppy, the quintessence of classic American style, evolved from the casual uniforms of the ‘preparatory schools’ of the ‘20s.
Gian Carla Espinosa Aritao | Sep 05 2018

It is the American dream that shaped a subset of fashion called preppy, a selection of clothes that is youthful, well-heeled, and expectant of success. The term itself is derived from “preparatory school,” where kids who wore uniforms adapted their khakis and madras well into adulthood.


Defining preppy

In the 1920s, the face of American fashion began to take shape when it took its cue from clean-shaven, privileged boys from Ivy League schools. These students were of a distinct class, unabashedly upper crust, and socialized within their own circles. Thus, most of them already knew each other before they even set foot in Yale, Harvard, or Princeton.

They had established codes and traditions, some of which related to the minute details of their uniform, such as which prints were acceptable on ties. Button down shirts, ties, and loafers were the standard garb. Sports were another major influence. It was not unusual for collegians to transition the attire of the tennis courts to social functions, as a sign of pride over their athletic accomplishments.

Photo of student by Michael Mars of Yale University. Yale Office of Public Affairs & Communications.

The appearance of success is so strongly related to this particular style of clothing that it spawned its own etymology of colors. Nantucket Red, a signature preppy hue, is a washed-out red that mimics the colors of painted wood found in Nantucket, New England, where the elite spend their summer vacations. There was an obsessive regard to the details of the clothes. The length of the hem, the roll of the sleeve, and the kind of cap worn all contributed to the regalia of prep. In what can be described as a bizarre mix of conformity and quirk, the style rebelled against rigid silhouettes. Though still outfitted conservatively to pay homage to tradition, students preferred cuts that were more casual and loose. Suit jackets, for example, lost much of their nips at the waist to allow for freer movements.


Grown-up preppy

A decade after the ivy-walled universities spawned these trends, students who wore them persisted in bringing their look back to the real world. Casual, athletic-inspired menswear became firmly ingrained in fashion. It was reinforced by the proliferation of brands that realized how marketable the look was. Labels allowed the trends to mature in order to fit them into the workplace. Brooks Brothers became synonymous with the style. The company introduced the diagonal repp tie, which it adapted from British regimental ties. Brooks Brothers’ decision to reverse the direction of the stripes became part of the look that would become a classic early on. By the 1950s, the repp tie was a staple in the preppy wardrobe.

There was also J. Press, a label that began in 1902 by selling items to college students by visiting  campuses by train. Unlike Brooks Brothers, which pushed trends to break them, J. Press made a conscious effort to remain faithful to the streamlined, slightly rumpled elegance of the preppy style.

 Mad Men, the hit cable television series set in an advertising agency in the ‘60s, renewed the interest in preppy style. Photo courtesy Lionsgate Television

The Kennedy men, John and Robert in particular, are quintessential preppies, bringing their Ivy League sensibilities to the world of politics. Though it took a Kennedy to give credibility to the perception that preppy was the dress of success, actors like Cary Grant and musicians like Miles Davis made it look cool. Common to prep style was the refusal to take oneself too seriously. Jackets were often unbuttoned to reveal a lining of patterns or bright pink. The designs were whimsical, embodied in classics like the special sailing pants designed by the clothier Chipp. The four-paneled garment featured one green and one red pants leg, meant to represent the port and starboard sides of a boat.


Evolving preppy

By the late ‘60s, Ivy League schools relaxed their admission policies. It was a time of great cultural and political ferment, with the assassinations of the Kennedy brothers and Martin Luther King, Jr. putting the United States in a somber mood. Styles evolved to embrace individuality through bell-bottoms and dashikis, putting the comparatively straight-laced, conservative preppy out of place.

It took several years before preppy reclaimed its place in fashion with the emergence of designer Ralph Lauren. He began as a salesman for Brooks Brothers, where he noted the passionate interest in fine, luxurious clothes. The philosophy stayed with him when he put up the company Polo in 1968, which began by selling clothes, but evolved to purvey a lifestyle.

Lauren used idealized, if not stylized, images of what the clothes represented. He designed not only for men but also for women and children, and introduced a home collection line that included sheets, towels, and furniture. His timing was impeccable, riding on the economic upswing of 1980s America and gratifying a national appetite for showy opulence.

A slew of other designers followed suit. One of these was Tommy Hilfiger, who favored the patriotic colors of red, white, and blue. His take on the new preppy—bold with large logos and moderately priced—was a hit. Hilfiger, both the designer and the brand, proved that old money was no longer a prerequisite to success.

The movie The Royal Tenenbaums inspired Tommy Hilfiger’s widely successful “The Hilfigers” campaign, luxurious clothes that fit closer to the body, the designer’s version of preppy. Photo courtesy of Tommy Hilfiger

Recent reincarnations of preppy offer the same aspirational perspective, said to be a factor for its resurgence. With many professionals left licking their wounds in the wake of bad economies, the pull of something familiar is undeniable. The clothes can look just as at home today as it did decades ago. They are not only practical, they are also associated with a more hopeful time.

Almost a century after its inception, preppy style is secure. The number of designers who incorporate seersucker and Bermuda shorts on the runway obliterates all doubt. While the new preppy is more diverse, it retains the nostalgia of more innocent times, which gives it its enduring and endearing quality.


First appeared in Vault Magazine Issue No.5, 2012