The Ultimate Preppy Listacle

With all the information out there about preppy style and history. We wanted to gather as much information as possible, then make it digestible and easily accessible — because if you want to learn the basics, or just impress people with your knowledge, that task should be easy.  

Without further delay, here’s everything you need to know about prep in a highly skim-able listacle.

The Story Behind Prep

  1. The first brands to create preppy clothes were J. Press and the Brooks Brothers. These brands initially only sold their clothes to the Northeastern collegiate, opening storefronts on various Ivy League campuses. It wasn’t until the 80’s that prep would become widely available via J. Crew, Ralph Lauren, and LL Bean.
  2. Preppy was sporty way back when. The clothes were designed to be worn at their favorite sporting events, like rowing, polo, and golf. In other words, preppy clothes were the upper-class equivalent of the modern day fan jerseys.
  3. The colors of summer were common in collegiate fashion. The brands catering to these elites incorporated the bright colors of Palm Beach into their apparel, since that was a common vacation spot for Northeastern Ivy League families. Hence, the preponderance of bright colors in contemporary prep.

 Quintessential Sweaters

  1. Argyle Sweaters: You can also call them golf sweaters. They have diagonal patterns, usually overlaid on diamonds.
  2. Cable-Knit Sweaters: This is a preppy staple that will never die. They’re made with cotton, wool, or cashmere.
  3. Cricket or Tennis Sweaters: These are also staples in any prep’s wardrobe. Invest in a fitted version for a youthful silhouette.

 Must-Have Jackets

  1. Barbour Wax Jackets: These are jackets inspired by hunting and horseback riding jackets. Perfect for a sporty-meets-sophisticated look.
  2. Navy Blazers: Designed for preps and available in a variety of styles, no prepster would be caught dead without at least one in his closet.
  3. Quilted Jackets: This is perfect for when the weather is cool and you’re going for a dressed down look.

 All The Accessories You Need

  1. Anchor Bracelets: This is a nautical accessory, through and through. Usually made with rope, leather, or sail cloth, a miniature anchor acts as a hook.
  2. Ribbon Belts: A tri-stripe belt is a simple accessory that adds just the right amount of fun to an otherwise serious ensemble.
  3. Regular Ties & Bow Ties: You can never go wrong with a striped bow tie. We’re also known for sporting ties with unconventional designs.

 Classic Shoes

  1. LL Bean Boots: This shouldn’t come as a surprise, since preppy was sporty way back when.
  2. Boat Shoes: Usually made of leather or suede, these are non-slip shoes made for sailing. Never ever wear socks with these!
  3. Loafers: Laceless and traditionally casual, loafers can also be worn in formal settings.
  4. White Buckskin Shoes: These are your all-things-summer companions. Pair them with linen or chinos for the perfect look.

 The Pants

  1. GTH Pants: Nauseatingly embroidered with nautical icons, general indifference towards haters is needed to wear these pants.
  2. Chinos: These are basically fitted khakis. The best pairs are made from cotton, though there are synthetic blends out there.

 The Usual Suspects (Shirt-wise)

  1. Oxford Button-Downs: Made by the Brooks Brothers to “casualize” the dress shirt, these are a must-have in any prep’s wardrobe.
  2. Polo Shirts: Also a preppy staple, this is the prepster’s alternative to the t-shirt.
  3. Rugby Shirts: These are favorites among prepsters, since they use bold colorful stripes and feature a white collar.

 Basic Fabrics

  1. Madras: A kind of lightweight cotton fabric, it’s used to make boat shorts and men’s jackets.
  2. Seersucker: Another kind of cotton fabric, this material is used to make summer suits, shorts, and pants.
  3. Tweed: A fairly heavy fabric, this is typically used in preppy winter-wear.


Ready to learn more about preppy style?   Getting your duds from Tailor Vintage puts you on your way.


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