8 Ways to Pull Off the Perfect Preppy Look

You don’t need to be a boarding school alum, have a country club membership, or play polo to adopt a preppy style. Wearing preppy clothing is about having a truly timeless look. It’s also a great way for men to integrate color into their wardrobes. If you don’t know the first thing about dressing preppy, and you’re concerned you might overdo it on the patterns or wear too many bright colors at once, don’t worry. Relax, grab a drink, and read on to discover the secrets of preppy style.

1. The sort-of-secret formula

Levent Kulu/Stringer/Getty Images

Pick a pattern to go with your solids | Levent Kulu/Stringer/Getty Images

Most preppy ensembles can basically be taken down to a simple formula: two solids + one pattern = preppy

Let’s say you are wearing navy chinos and a pink sweater. Underneath that pink sweater, choose a blue gingham button down. Wearing plaid pants? Pair them with a solid polo and a blue blazer. Don’t forget, when in doubt, brighter is better, but nothing takes the preppy cake more than Nantucket Red. 

2. Khaki is the preppy black

Man wearing khaki trousers

Man wearing khaki trousers | iStock.com

In The Official Preppy Handbook published in 1980, Lisa Birnbach writes, “It is the inalienable right of every man, woman, and child to wear khaki.” You can never go wrong with khaki pants. They can be formal or informal and coordinate with just about every other color on the spectrum. Think of khaki as the official “black” of preppy.

3. If it’s got a collar, holler!

Man putting on a collared shirt

Man putting on a collared shirt | iStock.com

If your shirt doesn’t have a collar, throw it out immediately (or just put it in the non-preppy part of your closet). The most important piece of any preppy wardrobe is a shirt with a collar. While most menswear brands make Polos, you can’t go wrong with the original Ralph Lauren Classic Polo Shirt (little pony, not the nouveau Big Pony). Brooks Brothers and Lacoste also make great Polo shirts.

When a polo is too casual but a dress shirt is too dressy, wear a patterned button down. The brighter and bolder, the better. New school preppy brand Vineyard Vines has a lot to choose from.

4. Shoes

Man wearing moccasin inspired boat shoes

Man wearing moccasin inspired boat shoes | iStock.com

A preppy man only needs three types of shoes. For most occasions, it’s a loafer (but never ever with socks). They can be a classic penny loafer style or even a driving shoe. For a more casual look, go for boat shoes. No, you don’t actually have to be at sea or on a lake to wear them. For rainy or snowy days, all you need are these classic boots from L.L. Bean.

5. Outwear

Man wearing a preppy coat

Man wearing a preppy coat | iStock.com

A well cut coat or jacket is all you need, and it will last you so long, you might even be able to pass it down to your child.

6. How to be preppy at work

Man wearing a suit with a pocket square and watch

Man wearing a suit with a pocket square and watch | iStock.com

You can express your inner prep in even the most conservative office as long as you keep it to a piece or two. For example, pair a navy blue suit with a preppy printed tie or bow tie. For some extra flare, add a pocket square.

7. Patterns galore

Plaid shirt

Plaid shirt | iStock.com

Nothing screams preppy more than a pattern. Whether it’s plaid, madras, gingham, seersucker, paisley, tweed, or anything involving seahorses, the right pattern sets the tone for the whole ensemble.

8. Lilly Pulitzer

A series of bright preppy fashion

A series of bright preppy fashion | iStock.com/iprachenko

Lilly Pulitzer is perhaps the epitome of prep. For many years, the clothing brand had a men’s line featuring signature patterned ties, swim trunks, and even blazers. Unfortunately, the line is no longer available (and if you are reading this over at Lilly corporate, can you please bring it back?), but you can always find vintage pieces on eBay. There are also several Etsy shops that use authentic Lilly Pulitzer fabric to make ties and bow ties. Wearing anything Lilly will color any true prep impressed.