The History of Vintage Preppy Style

by Sammy in , Comment — Updated May 27, 2024

Vintage Tag History: Levi's, Banana Republic, Betsey Johnson, Abercrombie & Fitch and MoreIn the 50s of the last century, graduates of prestigious colleges of New England, preparing future students of the Ivy League, brought their school wardrobe to just honed perfection so that their school uniform became not only the stylish symbol  but also the symbol of the lives of several generations, and easily stepped out of the youth subculture in the world of adults, and even high fashion. The name of this exquisitely-school style – preppy, from the English means«pre-college, preparatory». It is so called after elite preparatory school for American boys and girls from well-off families.

What’s the highlight of the preppy style? The ideal combination of formal, uniform clothes for everyday use and comfortable feelings. Ideologically, preppy is very close to smart casual, which also seeks to make formal, business-like style more interesting. But unlike democratic casual, it is focused exclusively on luxury, branded items. Preppy is an exquisite negligence of the “elite youth” that can afford clothes made of natural fabrics of the best and most prestigious designers. An interesting peculiarity is that this style spreads both on daily clothes and sports ones like tennis, lacrosse, golf.

Up to the 80s of the last century, preppy style remained to be the hallmark of youth from high society elite. Only after the book by Lisa Birnbach “Official Guide to preppy style”, where she expressed the seditious idea that anyone can be preppy, even if he is not a descendant of the family, that traces its roots to the founding fathers, the style reached out to the common people. Another surge in popularity of preppy style was several years ago on the screens of the TV series “Gossip Girl,” about the difficult everyday life of the contemporary representatives of the “elite youth”

The main features of preppy style are simple enough.

Clothing: club jackets, knitted vests, cardigans, turtlenecks, pullovers, blazers, trench coats, coats, shirts or oxford shirts, classic trousers, skinny pants, chinos. And do not forget the tie or butterfly.

Shoes: loafers, oxfords, derbies, brogues.

Hats: Trilby, fedora, beret or Tyrolean.

Prints: square, diamond, stripe.

Only natural fabrics: linen, tweed, cotton, wool, cashmere. Preppy colors: in the 50s, when preppy style just appeared, it was inclined to the more reserved, formal tones, but modern designers generously added  bright, unusual colors. Today, you can safely dilute your classic gray-white -Beige preppy pattern with deep blue, red, yellow and green.

All of the clothes must necessarily be made of natural materials and labeled by the most prestigious and expensive designers in the world. Your outfit should be no call: torn jeans, frilly accessories or ostentatious carelessness – all these are a taboo. Preppy means a clear, soft lines almost classic silhouette and a neat, well-groomed appearance. So forget about the beard, mustache, and stubble.

It is important to understand that the preppy is not just about fashion, but it is also a kind of subculture, a way of thinking and living. If you belong to the preppy way of life, you have to be educated, polite and punctual. Your manners and clothes should speak eloquently about your high social status. The fact that you are focused on success, elegance, a perfect college paper and education will mean a lot. Preppy is expensive but a discreet compromise between conservatism and comfort, it is confidence in yourself and your place in life.

Preppy style – icons:

Jacqueline Kennedy Onassis

Audrey Hepburn

Kelly Gray

Kate Middleton

Gwyneth Paltrow

And preppy style clothing is widely and successfully used in films and serials:


Carrie Diaries

Gossip Girl

Wild Child

Desperate Housewives (style of  Bree Van De Kamp)

Preppy style can easily be found in the collections of the following designers and companies:

Tommy Hilfiger

Vineyard Vines


Ralph Lauren

Marc Jacobs

Luella Bartley

Robert Everett: I am a freelance writer currently based in Chicago. Solving students career and university problems. Having interest in marketing and business. 

Leave a Comment