History of “Preppy” and Brooks Brothers: Democratizing of Style

I grew up surrounded by the quintessential “preppy” aesthetic. Monday through Friday, scores of uniformed children flocked up and down Madison Avenue to their respective single-sex private schools, often accompanied by a coiffed parent or nanny.

Each child donned at least one item from their closet of clean-cut, colorful, and modest J. Crew clothes (or Crewcuts, the children’s line). The schools required students to wear knee-high socks with ballet slippers for monthly concerts and school events. Monogrammed hair bows were all the rage.

When I arrived at Middlebury, I soon realized that people had differing versions of what “preppy” meant to them. To some, it was a polo shirt in lieu of a t-shirt. To others, it was a flowy LoveShackFancy skirt. I struggled to reconcile these differences with my own experiences growing up in the preppy capital of the world. I began to wonder if what I knew to be “preppy” was just simply outdated.

As a History major, I began to dig. Where does the word “preppy” even come from? Where did these clothes come from? Are they still around today, and, if so, why does “preppy” mean so many different things? To some, wearing a polo shirt and khakis is the pinnacle of preppy. To others, it is a fluffy pink dress. It is associated with wealth, intellect, or, to some, a lack of style.

For those who subscribe to the “preppy” look, you have Brooks Brothers to thank. Founded in 1818 by Henry Brooks, Brooks Brothers is the pinnacle of prep (1). Living in downtown New York, Brooks worked by the docs. The United States had been at war with the United Kingdom when The British–the former supplier of the U.S. fabrics–dumped piles of cloth into the water. Rather than taking this action as an insult, Henry Brooks decided to take advantage of the cloth. He decided to promote his company as a source of “ready-made” clothes, relying on the labor of young women in the city (2). Although their names were left out of the branding, these women molded Brooks Brothers into what it is today. Aside from being the outfitter for 40 American presidents, the clothing brand reinvented how we view fashion. Before 1818, wealthy families were dressed in custom-woven clothes. “Ready-to-wear” clothes were considered markers of a lower class, one that could not afford the time and fabric required to outfit themselves. After the emergence of Brooks Brothers, mass-produced clothes changed how Americans regarded style and shopping.

The term “preppy” hails from the 1920s Ivy League Preparatory Schools. Outfitted in Brooks Brothers, these well-off young men practically invented the style that I was so familiar with as a child. More casual than their wealthy parents but with an air of superiority, these men sought to establish themselves as affluent young men in society. Half sporty, half formal, Oxford cloth button-down shirts became a staple of the aspiring elite. They co-opted working-class clothes to fit their private school lives, and, in turn, turned preppy clothes into a staple of the intelligentsia. 

The clothes that constitute “preppy” have evolved since the 1920s. The term “preppy” seems to have been conflated with wealth. Any item with an absurd price tag (LoveShackFancy, anyone?) is deemed “preppy.” Looking historically, though, the original preppy clothes were made for working-class New Yorkers. Although elements of the past are still seen to this day at Middlebury (think “Just-Outside-of-Boston” parent at a lacrosse game), the preppy style has become a trend for the masses. One need not shop exclusively at Brooks Brothers, either. Button-downs, argyle sweaters, and pleated skirts are sold by a myriad of outfitters and can be bought at affordable prices. 

Today, preppy can mean so many things. To me, preppy is clean, subtle, and appropriate for most occasions. It is simple and elegant, yet durable and comfortable. From the Manhattan dockyards to Ivy League campuses, preppy clothing has defined generations of style. Though you will never see me in boat shoes or wearing the Brooks Brothers golden sheep logo, I still incorporate elements of my preppy upbringing into my closet. Some tops just do look better layered with an Oxford pinstripe shirt. 

Footnotes:

(1)Schneider, Sven Raphael, et al. “Brooks Brothers - The History of an American Haberdashery.” Gentleman's Gazette, 16 Mar. 2020.

(2) “Where Have All the Preppies Gone? with Avery Trufelman.” Spotify, You're Wrong About, 28 Nov. 2022.