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The Ultimate Guide to Preppy Style


What come’s to mind when talking “Preppy”?  One might think it’s only for those Ivy League school graduates or Northeastern academics, but as we all know its more than that. While it is originated from a subculture of upper-class young college students born into old money in the Northeast of United States, today’s prep culture has transcended into a lifestyle that covers speech, vocabulary, dress, manners and etiquette adopted from upper-class Northeastern families.

The prep culture is still very popular in the Northeastern regions, but has spread into variety of areas often thought of as classic American culture. A wide net of traditional colors, apparel, and patterns inspire the modern flavor of “Preppy Style”. Brands like Brooks Brothers, J.Crew, LL Bean, Ralph Lauren typically provide nautical yet clean images of the typical preppy look. We’ve taken inspiration from some brands around the world and put a Connecticut twist on the design, look, and feel to give Tailor Vintage that special something… As most prepsters know, style is more than just bow ties, boat shoes, and madras. Modern fitted flavors can refresh and liven up classicism preppy prints.  One of our specialties, comfy yet timeless french terry's should be a constant in any gentlemen’s wardrobe.

Just as bikers wear leather and tattoos, rockers wear tight leather and band shirts, and cheerleaders wear pink, preps has their own signature looks. Defined by smart crewneck sweaters, oxford button-down and polo shirts, chinos, navy blazers and refined accessories, the preppy look now is about as unapologetically all-American as it gets. While there is technically a right and wrong way to do prep, there is certainly nothing wrong with playing around with the details and adding your own twist. Style is about individuality after all. The most important thing to remember is the core essence, the preppy style is defined not just by the clothes but the attitude that goes along with it. So gentlemen, by all means dress well, but don’t forget to carry yourself well too.


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