The Ultimate Guide to Dressing Preppy for Men

Last updated: February 13, 2022

Dressing preppy is synonymous for most people with tennis courts, wealth, and class on the one hand, and frat movie corniness on the other.

Just because you want to dress preppy, doesn’t mean you can’t maintain a look flush with modern appeal.

Think of this post as a “starter kit” for people that are more interested in looking like they are a part of a college campus in New England and listen to Vampire Weekend nonstop.

It has some of the textbook “prep” essentials, along with some unique recommendations.

We recommend that you’ll have to adjust this wardrobe to your location and personal style. For instance, if you live in the Midwest, you’ll look out of place wearing boat shoes and salmon pink shorts.

Many preppier brands can be pricey. But, there are ways to put together a wardrobe over time that reeks of “probably was on the rowing team,” without breaking the bank.

Quick jump:

Prep Style Characteristics

Prep style is based on students living in the college preparatory academics within the Northeast. Rural life (even if its a quick escape from the daily city job), Ivy Leagues, and sailing all played a part in creating the “preppy” image in fashion.

Start by adapting your preppy style towards a more youthful and modern silhouette. Using inspiration from the traditional preppy apparel, patterns, and colors should help create a modern design.

Fitted styles will refresh the classic preppy prints while tartans and ginghams create a more youthful look.

You can wear polos to accentuate your casual look, but continue to use traditional colors to have a more refined touch.

Ivy Prep Wardrobe Staples

Shirts

Bottoms

Outerwear

Footwear

Accessories

Here are the most common preppy accessories:

  • Cuff Links
  • Scarves
  • Watches
  • Leather belt
  • Monograms
  • Pocket square
  • A pair of Ray-Ban Wayfarer or tortoiseshell Glasses

For those that play by a stringent set of rules, it’s important that your belt and shoes match, especially if you’re going to formal events. While the shades don’t have to be perfectly matched to a tee, they should at least be within the same spectrum.

While you can experiment with the prep style, there are some accessories that are best kept simple. For example, cufflinks can be worn in silver or gold accents, and they create the right amount of subtle flair.

Pocket squares and scarves are a great way to complete your outfit and show that you’ve placed some effort behind your look. You have an unlimited set of options as bold prints, neutral tones, and bright hues are all acceptable.

Experimenting with Patterns, Colors, and Textures

While prep clothing is built on classics, there is almost always room for experimentation. Whether you want to add color or have an eclectic style, playing around with different patterns, colors, and textures will give your outfit a fun and modern look.

There is an endless amount of fabric options to choose from. It’s up to you how you want to experiment with them. Suede, velvet, linen, corduroy – all of it is fair game.

Velvet is a great option, as it gives you a unique edge while showing class, and looks good when paired with a pair of penny loafers or a nicely-fitted blazer. Blue, red, and black shades help compliment velvet seamlessly. Tweed is another option to consider as it provides an alternative to the standard navy blazer while still keeping the preppy look.

Don’t be afraid to add bold and bright colors to the mix. We’re talking about wearing pastel pinks, greens, and bright blues, just to name a few. While wearing striking colors can be intimidating at first, it helps you develop your own fashion sense and not look like everyone else.

When mixing your patterns, less is more. Having a combination of 2 patterns (no more than 3) is the ideal amount, and prevents you from looking like an eyesore.

Prints look best when they are separated in broken hues, and colors should stay in the same color group. One good example would be pairing a plain colored shirt and a Fair Isle Sweater within the same color scheme.

Best Preppy Clothing Brands

Ready to step your preppy clothing game up? Here are the time-tested best preppy clothing brands.

Gant

Gant was founded in 1949 and is now a part of the Gant Corporation. Gant offers a wide range of clothing, such as shirts, jackets, sweaters, pants and accessories.

Gant has been at the forefront of fashion for over 60 years. The company has always been known for its attention to detail and quality garments. Gant is headquartered in New York City and operates more than 300 stores around the world.

The company was founded by Walter W. Ahlgren who wanted to create a shirt that would be perfect for every occasion and that would look good on every man.

The company’s first store opened in 1950 on Madison Avenue in New York City with just 12 shirts on display.

Orvis

Orvis is a US-based company that sells high-end clothing, gear, and sporting goods. They offer a wide variety of products for men and women.

The company was founded in 1856 by Charles F. Orvis (1837-1914). He opened its first store in Manchester, Vermont. The store sold fly fishing tackle and other fishing gear. The business grew quickly and the company started to sell clothing as well as sporting goods like tents, backpacks, and camping equipment.

J.Crew

J.Crew is an American clothing and lifestyle company that was founded in 1983. The company’s headquarters is located in New York City, with retail stores operating around the world.

J.Crew sells classic and contemporary men’s and women’s clothing, including tailored garments, sportswear, outerwear, dresses, skirts, sweaters, jeans and shirts; footwear; etc.

G.H.Bass

G.H.Bass is an American shoe company that was founded in 1876 by George Henry Bass, who emigrated from England to the United States in 1868 and started his own shoe company with his three sons, John, George Jr., and Alfred, in Lynn, Massachusetts.

The company was originally called Bass & Company but changed its name to G.H.Bass & Co in 1890 when it became a private corporation after the death of George Sr.. G.H Bass has since grown into a global footwear brand with more than 500 stores around the world and over 3,000 employees worldwide

L.L.Bean

L.L. Bean is a family owned company which has been in business for over 100 years and is best known for its outdoor clothing, footwear, and accessories.

The company’s most popular products are its rubber-soled shoes and its signature boots which are still manufactured by artisanal craftsmen in Maine.

Barbour

Barbour is a British clothing company that was founded in 1894. It has been supplying men and women with high-quality outerwear and sportswear for more than 100 years.

The company’s headquarters are still in the original factory on the outskirts of their hometown, South Shields, England.