What Does It Mean to Be Preppy?

“Preppy” is often associated with a certain style. We all know the look; cable knit sweaters, rugby shirts, boat shoes and seersucker. Without a doubt, these styles are found in the closets of all preppies. However, to characterize preppy as just a way some people dress is a grave mistake. There is so much more to the preppy lifestyle than simply clothing. In this article we’ll dive into what it really means to be preppy, so whether you are a life-long preppy or are just starting to ask how you can become more preppy, I hope you are able to take something meaningful away from these thoughts.

The hobbies of preppies may be the aspect of their lifestyle which is second most recognizable (their dressing habits being the most). It is clear that their hobbies are not to be confused with 

the adrenaline-fuel adventures of skydivers and cliff jumpers. Instead, preppies value a sort of “refined” adventure that is characterized by modest physical activity, but more importantly a sense of exploration of the world.

Consider the activities most associated with the preppy lifestyle, hobbies such as sailing, golfing, fishing, hunting, hiking and camping. Each of these hobbies involve exploring the world in a new way. You are unlikely to chart the exact same path multiple times while sailing, hunting or camping. You may play the same golf course, hike the same trail, or fish in the same spot time and time again, but the experience each time is certain to be different. Preppies embody a sense of adventure that drives them towards these sorts of activities. 

What does this mean if you are someone trying to become more preppy? It’s simple: embrace adventure in your life. There are no specific hobbies you need to take up for this to be the case. If golf is too expensive for you, try disc golf. If you don’t live near a lake or the ocean, try kayaking in local streams or rivers. No matter where you live, you can live a preppy lifestyle by seeking out refined adventure in your everyday life, and enjoying your exploration of the world.

Tradition is an under appreciated element of the preppy lifestyle. This is unfortunate, because in reality it is a very important aspect. Preppies are marked by a respect for tradition and history. This is most evident in the universities they attend.

The universities preppies are known for attending are the Ivy League schools. Particularly Harvard, Yale and Princeton. These schools are recognized for their academic prestige, but beyond that they are also institutions rich in history. Founded in 1636, 1701 and 1746 respectively, they all predate the independence of the United States of America. Their architecture and libraries reveal previous eras of American history. This historical significance is what draws preppies to their programs each year. They do not just value the education they will receive or the jobs they will get with their degrees, but also the chance to join institutions steeped in history.

What does this mean if you are someone trying to become more preppy? Seek opportunities to reflect on history and tradition in your life. If college is still ahead of you, consider more than just the cost of the program. Consider the prestige and historical significance of the school. Ivy Leagues may be difficult to attend for financial or academic reasons (they have a tendency to be exclusive for for both reasons), but there are plenty of liberal arts colleges with rich histories, beautiful architecture, and affordable tuition. If school is behind you, find local museums to visit, or plan travel to places with historical significance. Most simply, read classic literature to gain insight into previous generations. Books like The Great Gatsby and To Kill A Mocking Bird are a great start.

This may seem the same as the previous section, however I believe there are important differences. Nostalgia is a quintessential element of the preppy lifestyle. Preppies are not in a rush to integrate modern technology into every aspect of their life. This is evident through their obsession with old Jeeps and their tendency towards exposed wood in their interior design.

What does this mean if you are trying to become more preppy? It is easy to add a little more nostalgia to your life. Identify areas where you can go without modern conveniences. Grind your coffee with a hand grinder, write in a pen-and-paper journal or decorate your house with thrifted pieces (though let's not get carried away with this one). 

This article doesn’t come close to covering all the elements of what it means to be preppy. There are too many of those for any single paper to cover. What it does, I hope, is establish that the preppy lifestyle goes far beyond simply dressing a certain way, and if you want to become more preppy, you can do so without buying any new clothes. Before concluding, I want to emphasize that the characteristic fashion of preppies is important. Wearing high quality fabrics from established brands like Brooks Brothers, J Crew, and L.L. Bean is a real element of the preppy lifestyle, it’s just not the only one. Being preppy is not just about wearing seersucker or boat shoes—it’s about cultivating a lifestyle that values exploration and adventure, respects history and tradition, and indulges in nostalgia for its own sake. Clothes may signal preppiness, but they’re not where it ends.

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