The Rise of the Preppy

Culture | December 27, 2018

President Kennedy Playing Golf at Hyannis Port, Massachusetts wearing a casual, preppy look. Source: (GettyImages)

The elite, private, preparatory schools of New England developed their own style of clothing that, at least for men, stretched back to the 1920s and 1930s. But it was in the 1960s that this style, the Preppy style, became more mainstream and helped to make many people fall in love with blue blazers and khaki trousers. Let’s look at the rise of the Preppies. 

Source: nineteenfortythree.blogspot.com

The Kennedys Made Preppy Cool

It was the Kennedy family, with their aloof East coast wealth and privilege, that made preppy fashion a sought-after look. Young men wanted to emulate the cool, confident sophistication of John and Bobby Kennedy, and young women were attracted to the casual classic look of Jackie Kennedy. 

Source: mwfilmnewsroom.blogspot.com

The Preppies were Polar Opposite of Hippies

The 1960s might be known for the hippie style of clothing, characterized by eclectic, colorful, bohemian vibes, but preppy fashion was gaining ground in the sixties. Preppies were all things that hippies were not…conformists, traditionalists, and modest. 

Source: ivy-style.com

Preppies were all About Navy

Preppy fashion has not changed drastically over time. In stark contrast to the psychedelic fashion of the groovy sixties, the styles that were popular in the Ivy League and prep schools of the Northeast revolved around the blue blazer. The dashing blazer, worn by both men and women in the sixties, often featured an emblem on the breast with a school crest or family coat of arms. It was all very proper and refined. 

Even Brigitte Bardot embraced the preppy striped sailing shirt. Source: bbc.com

The Striped Sailor Shirt

Sailing was a popular activity for the students in elite schools so it is no wonder that the classic sailor t-shirt, a long-sleeved striped shirt, was popular preppy wear of the sixties. The shirts were white with navy blue, black, or red stripes and had gold buttons on the sleeves or shoulders. 

John Kennedy was super casual in khaki shorts. Source: mashable.com


Neutral khaki slacks with pleats were a staple of preppy wear. In the sixties, the khaki trousers featured deep pleats and wide legs. When paired with a navy blazer, the khaki pants became, quite literally, the uniform for prep school students. 

Arnold Palmer helped make the polo shirt a preppy favorite. Source: myhero.com

Polo Shirts

Collared polo shirts were worn by preppies in casual situations, like on the golf course or tennis courts. But the polo shirt was dressier than the traditional t-shirt and could be worn with a navy blazer for a snappy casual style. 

Source: pinterest.com


Preppies were mad for plaid in the sixties. The school uniform worn by female students at the elite prep schools often included a pleated plaid skirt. But plaid wasn’t just for skirts. Plaid button down shirts were worn underneath solid colored sweaters, with the plaid collar, cuffs, and tail showing for a pop of pizzazz. In the 1960s, it was fashionable to match your plaid clothing with plaid accessories so all your plaid was consistent. 

Source: oxfordclothbuttondown.com


The preppy look was complete when you added a pair of well-made loafers to the outfit. For girls, penny loafers were popular. These were often worn with knee socks and plaid skirts as part of the prep school uniform look, but could also look good with trousers. For men, tasseled loafers or boat shoes helped to bring the elite sporty look to the masses. 

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Karen Harris


Karen left the world of academic, quitting her job as a college professor to write full-time. She spends her days with her firefighter husband and four daughters on a hobby farm with an assortment of animals, including a goat named Atticus, a turkey named Gravy, and a chicken named Chickaletta.