The Ultimate Guide To Dressing Preppy For Men

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.

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.


Don’t Take it Too Literal

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.


Here are the most common preppy accessories:

  • Cuff Links
  • Scarf
  • 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.

Wardrobe Staples


Oxfords are the default shirt style for a prep wardrobe. Pale pink or light blue stripes work well.

Recommended: Brooks Brothers


Good for the fall/winter/early spring. For instance, the LL Bean Nordic Fisherman is a classy sweater within the prep world.

Recommended: LL Bean

Hunting Jackets

These jackets don’t need that much of an introduction and make a good addition to your fall wardrobe.

Recommended: Barbour


Flannel is the go-to option for colder weather, especially if you live near water.

Recommended: Backcountry

LL Bean Boots

These boots fit the prep look and feel comfortable on your feet. Get the insulated ones if you want to remain warm.

Recommended: LL Bean

Boat Shoes/Moccasins:

Good for casual shoes and can be worn anywhere.

Recommended: Sperrys


Madras adds complexity and color to your outfits. If you’re confident in your prep gear, try giving this staple a look.

Recommended: Brooks Brothers

Navy Blazer

This is a staple choice for most business casual apparel. When wearing a navy blazer, try to match it with a neutral color that contrasts with it well (i.e., white, gray, etc.).

Recommended: Brooks Brothers


When building your “prep look,” don’t be afraid to use vibrant colors and different fabrics.

Once you have a solid foundation, you can begin to experiment and start wearing clothes that both fit and represent you.