Ultimate Preppy Guide – Origins, Subculture, Values, and More

What is Preppy?

Short for ‘preparatory,’ the term ‘Preppy’ describes a subculture that originated in the early 1900s in northeastern American preparatory schools for boys, encapsulating values, activities, mannerisms, and ways of dressing.

Culturally, ‘Preppy’ signifies well-educated, well-connected, affluent people with high socioeconomic status.

The Origin of Preppy

Preppy subculture originated in the early 1900s in northeastern American preparatory schools and universities attended by upper-class students.

Early American education institutions followed the model of British preparatory schools and universities regarding education, uniforms, and activities, hence the subculture’s roots in British traditions.

The influence of British culture goes beyond activities, traditions, values, mannerisms, and lifestyle, impacting the school attire and pupils’ ways of dressing.

However, the Preppy subculture as we understand it nowadays was shaped by the social and cultural practices of America’s upper class in the late 19th and early 20th centuries.

Hence, the ‘origin of Preppy’ discussions revolve around American educational institutions and the three main educational areas credited with the creation and evolution of the Preppy fashion and lifestyle.

1. New England

The Home of Ivy League Preppy

New England is a northeastern region of the United States comprising the states of Maine, Vermont, New Hampshire, Massachusetts, Connecticut, and Rhode Island and home to Ivy League universities.

The first usage of ‘Ivy’ regarding a group of colleges is found in New York Herald Tribune’s October 14, 1933 edition, where sportswriter Stanley Woodward describes the football season:

“A proportion of our eastern ivy colleges are meeting little fellows another Saturday before plunging into the strife and the turmoil.”

By the end of the 1800s, planting Ivy at the New England colleges’ buildings became a practice named “Ivy Day.”

2. Upper-Midwest

The Home of Northern Preppy

The Upper Midwest is a region in the northern portion of the United States comprising the states of Iowa, Michigan, Minnesota, North Dakota, South Dakota, and Wisconsin.

The Upper Midwest regions, particularly Michigan and Wisconsin, with great lakes and cold winters, played an equally important role in developing the Preppy subculture and lifestyle.

3. American South

The Home of Southern Preppy

In the context of Preppy, the American South refers to the Southeastern United States, particularly North Carolina, South Carolina, Georgia, and Virginia.

The American South’s warm and humid climate and cultural traditions based on community, manners, formality, and refinement gave birth to the Southern Preppy look and lifestyle.

Each region contributed to developing the Preppy culture and style by reflecting local customs, lifestyle, and climate.

Who Are the Preppies?

Preppy people, ‘Preppies’ or ‘Preps’ refers to a subgroup of the American upper and upper-middle class associated with the Northeastern part of the United States.

Found across various age groups, Preppies are from affluent backgrounds related to or descendants of, old-money families with a long history of attending prestigious preparatory schools and Ivy League universities.

Geographically, early Preppies are connected with affluent Northeastern suburbs, New England coastal towns, parts of the Upper Midwest, and the wealthiest spots of the American South.

Yet, regardless of age, nationality, or location, Preppies are people with similar dressing, fashion styles, values, interests, and activities.

Preppy Values

Preppies’ values and lifestyles are deeply connected to their activities rooted in the subculture’s historical and socioeconomic background.

Some of the subcultures’ core activities revolve around higher education, sports, fashion and arts, philanthropy, and etiquette.

1. High Education

Preppies value education highly, particularly in prestigious preparatory schools and Ivy League colleges.

Attending esteemed preparatory schools, colleges, and universities, participating in academic clubs, and preparing for successful careers in law, business, or medicine are all central to the preppy lifestyle.

2. Sports and Recreation

Any preparatory school curriculum includes sports of British origins, such as polo, tennis, rugby, and rowing.

Over time, these sports have become critical activities at the core of an active and healthy Preppy lifestyle.

According to the ‘Preppies value book,’ these sports require sportsmanship, camaraderie, competitiveness, and being a team player.

3. Etiquette and Manners

Influenced by traditional upper-class etiquette and high education, Preppies are known for their courteous mannerisms.

Language is also important, as in the U.S., Preppies’ speech is characterized by a specific accent known colloquially as the ‘Locust Valley Lockjaw’ or the ‘preppy lisp.’

To preppies, good manners and proper etiquette signify a classic upbringing, tradition, heritage, and stylistic sophistication.

4. Tradition and Conservatism

To Preppies, tradition means connections to their roots, historical heritage, and upper class, reinforcing their sense of identity and continuity.

As such, most Preppies lean towards conservatism regarding behavior, political views, and fashion.

5. Social Gatherings

Preppies engage in social events within their social circle, such as parties, dinners, and charity galas.

These events aim to maintain a sense of decorum and decency in keeping with their respect for old traditions and good manners.

6. Community Service

Community service and philanthropy are part of Preppies’ commitment to social responsibility.

Some of the most popular activities are volunteering at local organizations, participating in charity events, or donating.

With a deep sense of belonging, shared values, and social responsibility, Preppies give back to their communities through charitable activities and volunteer work.

7. Business and Travel

Business and traveling are quintessential to the Preppy lifestyle.

Preppies combine business with traveling in affluent-class vacation spots such as Martha’s Vineyard, Nantucket, or the Hamptons, or traditional places where the Preppy subculture draws roots, such as Oxford and Cambridge in the U.K.

8. Arts and Culture

Knowledge and appreciation of fine arts are at the core of the Preppy subculture and lifestyle.

As such, Preppies are interested in the arts and have a propensity for classical music, ballet, and theater.

Some popular Preppy activities include attending theater performances, visiting galleries, reading art books and style magazines, and listening to classical music.

Preppy Way of Dressing

The preppy way of dressing requires representative clothes, shoes, and accessories – according to the Preppy aesthetic.

Also, ideally, the outfits are put together with clothes and accessories from renowned Preppy clothing brands like Ralph Lauren, Brooks Brothers, Lacoste, Tommy Hilfiger, L.L. Bean, and J. Crew.

Aligning with Preppy vocabulary, etiquette, and mannerisms, Preppy outfits always depict a classic, clean-cut look in daily life or sports.

Most Influential Preppy Figures

Some of the most influential people known for significant contributions to the Preppy subculture are:

• F. Scott Fitzgerald (Writer):

Fitzgerald’s novels, notably ‘The Great Gatsby,’ have been influential in depicting the lives and styles of the American upper class in the early 20th century.

• John F. Kennedy (Politician):

Brought up in New England’s cultural context and Ivy League educated, the 35th President of the United States was a crucial Preppy subculture figure.

Kennedy’s dressing style of thick chinos, polo shirts, and boat shoes is synonymous with the early Ivy League Preppy aesthetic.

• Lisa Birnbach (Author):

Birnbach’s 1980 book, ‘The Official Preppy Handbook,’ is known for having an in-depth look at Preppies and their lifestyles.

Often sarcastic, it remains a reference to the paper in understanding the subculture to this day.

• Ralph Lauren (Fashion Designer):

Inspired by the sport of polo and the lifestyles of the British elite, Lauren’s fashion line, Polo Ralph Lauren, has played a significant role in popularizing the Preppy style.

• Brooks Brothers (Fashion Retails):

As America’s first clothing retailer owner, Brooks Brothers introduced essential Preppy clothes to the American public, such as the button-down Oxford shirt, seersucker, and madras fabrics.

• Tommy Hilfiger (Fashion Designer):

Hilfiger’s fresh designs in the ’80s and ’90s helped to update and democratize the Preppy style, making it accessible to the broader public.

• Gwyneth Paltrow (Actor):

The actress and lifestyle guru Gwyneth Paltrow exemplifies the modern Preppy look and lifestyle via her brand, Goop, and fashion choices.

• Reese Witherspoon (Actor):

Draper James, the actress’ fashion line, is renowned for launching Preppy-style outfits depicting Southern style variation and its unique charm.

Preppy Books, Movies, Series, and Music Bands

There are several influential Preppy movies, books, series, and songs that have contributed to the creation and development of the Preppy subculture.

• The Great Gatsby (Book and Movies):

The Great Gatsby is F. Scott Fitzgerald’s classic novel, and film adaptations depict the opulence and fashion of the Jazz Age, almost like a manual for those interested in the extravagant side of the Preppy subculture.

The following adaptations of F. Scott Fitzgerald’s classic novel comprise lavish depictions of 1920s upper-class style, greatly influencing the preppy aesthetic.

• The Catcher in the Rye (Novel):

J.D. Salinger’s novel, The Catcher in the Rye, portrays preparatory school culture and has become a literary classic, influencing perceptions of the disillusionment and rebellion that can exist within the Preppy subculture.

• The Official Preppy Handbook (Book):

Lisa Birnbach’s 1980s book, The Official Preppy Handbook, has a satirical but severe look at the preppy lifestyle and is seen as the manual of what it meant to be Preppy.

• Love Story (Movie):

Love Story is a 1970 film that established the Preppy style as shorthand for elite American good taste by depicting the lives of Ivy League students.

• The Preppy Murder (TV Movie):

The Preppy Murder is a TV movie based on a true crime that highlights the darker side of the Preppy subculture in 1989.

• Gossip Girl (T.V. series and Books):

Gossip Girl is a popular series that covers a group of preparatory school students from New York City and their fashion wardrobes.

By portraying the lives of elite Manhattan teenagers, the series reached immense popularity and shaped the modern perception of Preppy style and culture.

• Dead Poets Society (Movie):

Dead Poets Society takes place in an elite preparatory school for boys and depicts rebellion within the constraints of a traditional Preppy institution.

The movie recreates the Preppy subculture’s origins, influencing how the general public understands it.

• Vampire Weekend (Music Band):

Vampire Weekend is an American rock band from New York City, formed in 2006, had their first album heavily influenced by Preppy aesthetics.

Their music and dressing style brought a renewed interest in the preppy style and lifestyle to younger generations and sparked an interest in the Preppy subculture in the 2000s.

• Prep (Book):

Curtis Sittenfeld’s best-selling novel, Prep, provides an in-depth and relatable look at a prep school culture, making it accessible to a broader audience.

The book dives deep into the boarding school culture while showcasing the intricacies and unexpected nuances of the modern Preppy subculture.

• The Princess Diaries (Books and Movies):

Meg Cabot’s series, The Princess Diaries, and the resulting movies present an average high school student who transitions into a polished princess by incorporating Preppy style and etiquette elements.

The movies gained global popularity for embodying the grace, elegance, and etiquette associated with the Preppy subculture.

• Gilmore Girls (T.V. Series)

Set in a picturesque and quintessentially preppy New England town, Gilmore Girls follows a mother-daughter duo and their laid-back, accessible version of the Preppy lifestyle.

• Cruel Intentions (Movie)

Cruel Intentions‘ portrayal of a decadent and manipulative side of preparatory school culture has turned it into a subculture favorite.

• Clueless (Movie)

Despite being set on the West Coast, Clueless popularized Preppy fashion in the 90s and influenced how the general public understands and adopts Preppy dressing styles.

• Legally Blonde (Movie)

Legally Blonde features a determined, fashion-conscious sorority girl at Harvard Law School and her bright, fun, feminine Preppy style twists.

Preppy Communities

Preppy communities that reflect the subculture’s interests, values, and lifestyle can be found offline (in real life) and online on the internet.

Best Preppy Colleges and Schools

The Preppy subculture is associated with elite preparatory schools’ of the mid-20th century, their uniforms, and activities.

The uniforms had a British-inspired  ‘country clothing’ style mixed with sports apparel for golf, yachting, rowing, tennis, rugby, and horseback riding.

In the Northeast, they are called the ‘Ivy League group’ and are comprised of Harvard, Yale, Princeton, Columbia, Cornell, Pennsylvania, Brown University, and Dartmouth College.

In the Upper Midwest, the University of Michigan – considered one of the few public Ivies – played an essential role in developing the Preppy subculture.

From the American South, the University of Virginia‘s architectural style and reputation as a bastion of Southern tradition was critical in propagating the Preppy subculture and lifestyle.

Other Preppy schools and colleges that participated in the creation and popularity of the Preppy subculture are:

• The Lawrenceville School (Lawrenceville, New Jersey)
• St. Paul’s School (Concord, New Hampshire)
• Groton School (Groton, Massachusetts)
• Phillips Academy Andover (Andover, Massachusetts)
• Phillips Exeter Academy (Exeter, New Hampshire)
• Choate Rosemary Hall (Wallingford, Connecticut)
• Hotchkiss School (Lakeville, Connecticut)
• Deerfield Academy (Deerfield, Massachusetts)

Many of these institutions are still active and known for continuing to foster Preppy values and lifestyles.

Online Gathering Places

Preppies are active on social media, preppy group pages, subreddits, and dedicated online forums.

Here are 10 of the most popular online gathering places for Preppies.

• Preppy Instagram Accounts – Preppies often follow and engage with popular Instagram influencers representing the preppy lifestyle. @KJP (Kiel James Patrick) and @SarahKJP (Sarah Vickers) are great examples of Instagram accounts promoting the Preppy image and ethos through fashion and lifestyle choices.

• Preppies on TikTok – The preppy community is very active on TikTok, driven by influencers that use their accounts as platforms for followers to watch videos about preppy activities, aesthetics, outfits, etc.

• Reddit Preppy Communities – Subreddits like r/NavyBlazer and r/Preppy provide a platform for users to discuss preppy fashion, lifestyle, and culture.

• Facebook Preppy Groups – Many Facebook groups are dedicated to the Preppy style and subculture, where users can share ideas and engage in discussions. Examples include ‘Preppy Is How We Dress‘ and ‘The Official Preppy Handbook Fan Club 2.0.‘

• Preppy Fashion Blogs – Most Preppies follow blogs dedicated to preppy fashion. These include Ivy Style (www.ivy-style.com), The College Prepster (www.carlytheprepster.com), and Classy Girls Wear Pearls (www.classygirlswearpearls.com)

• Preppies on LinkedIn – Given the emphasis on professional success within the Preppy subculture,
  LinkedIn serves as a critical platform for networking and sharing professional achievements.

• Preppy Online Forums – Forums, like Ask Andy About Clothes, have sections dedicated to preppy style and lifestyle discussions where users can ask questions, share ideas, and engage in discussions.

• Preppy YouTube Channels – Preppies might follow YouTube channels focusing on preppy dressing styles, such as “@preppylife3973” or “@Kellyprepster.”

• Pinterest – Pinterest is a popular platform for sharing visuals related to preppy style, home decor, travel, and lifestyle. Users can follow boards dedicated to preppy style or create their own.

• Tumblr – Several Tumblr blogs are dedicated to preppy styles, like ‘The Classy Life‘ and ‘The Preppy Blonde.’