17 Best Preppy Clothing Brands for Guys (2023 Guide)

Looking for a list of the best preppy men’s clothing brands? We’ve got you covered!

Every guy has at least some idea of what “preppy” looks like. However, you might not be familiar with the nuances of this aesthetic.

Today we’ll cover the basics of preppy attire and run through some of the best preppy clothing brands for men. 

What is preppy clothing?

The preppy aesthetic was born out of Northeast college preparatory schools (hence the name).

Despite its upper-crust origins in the early 1900s, this aesthetic achieved huge popularity from the ’50s through the ’80s. Today, while perhaps less ubiquitous than a few decades ago, the preppy look remains popular to this day. 

In this guide, we’ll introduce you to the preppy clothing brands you need to know — from old-school classics like Brooks Brothers to more modern takes like Rowing Blazers. Next, we’ll cover where to find preppy shoes and conclude by answering common questions about this aesthetic. 

Classic Preppy Clothing Brands

Starting around 1912 and coming out of prestigious Northeastern universities, the history of preppy style goes back to the “Trad” and “Ivy” schools of dress.

With the help of a few major brands that made the style accessible to American men from all backgrounds, it would be another four decades or so before the preppy look really came into its own.

Probably the best way to think about “classic” versus “modern” preppy clothing brands is by paying close attention to when the brand was founded.

As a general rule, the older the brand, the more classic its look and feel. With that in mind, let’s look at some of the most iconic preppy clothing brands.

Brooks Brothers

Founded all the way back in 1818, Brooks Brothers is the oldest continually operating clothing brand in the United States. For generations, this company has been defining East Coast style from their New York headquarters. 

Brooks Brothers has long been the go-to brand for guys looking to build an entire preppy wardrobe. There’s a good reason why. Even though they’re considered a very “traditional” brand today, Brooks Brothers has been responsible for many wardrobe innovations throughout its long history.

This brand pioneered the pink dress shirt for men, argyle socks, the madras cotton pattern, and lightweight summer suits — all standbys in the preppy wardrobe. If you want to get all your outfits in one fell swoop, Brooks Brothers can make it happen.

Pendleton

The Portland, Oregon-based Pendleton Woolen Mills has been making the finest quality wool blankets, shirts, and accessories since 1863.

And while they’re quite a ways away from the East Coast Ivy League schools that defined the preppy style, the distinctive look and feel of Pendleton’s shirts and suits have earned them lasting popularity.

Check out their Iconic Pendleton collection for a curated selection of colorful clothes that made them a part of preppy style for the fall and winter.

Barbour

Officially registered as J. Barbour & Sons Ltd., this British company’s claim to fame is its iconic jackets and outerwear.

Their top-notch waxed jackets and coats have been in production since 1894, making the sort of heritage pieces favored by icons of menswear such as Steve McQueen. 

Be sure to check out their understated polo shirts while you’re perusing their broad selection of outerwear.

L.L. Bean

Ever wondered about the “L.L.” in this company’s name? That’s short for one of the coolest names you’ll ever read: Leon Leonwood Bean, the company’s founder.

L.L. Bean has been around since 1912, offering an expansive selection of apparel and outdoor gear for discerning men and women.

Their outerwear has become a go-to choice for completing the preppy aesthetic in cold weather.

GANT

Founded in 1949 by Bernard Gantmacher, a Jewish immigrant from Ukraine, GANT gained notoriety in the United States for the fantastic quality and attention to detail in their dress shirts. 

They became so popular that GANT was able to secure a contract with Yale University to produce exclusive shirts for them in the 1960s. 

As with many menswear retailers, this company now offers a complete line of clothing options; but I’d mainly just stick with their dress shirt offerings for an authentic preppy look.

Lacoste

Founded in 1933 by French tennis player Jean René Lacoste and his business partner André Gillier, Lacoste has been a major force in adding a “sporty” look and feel to the preppy wardrobe. 

Inspired by Lacoste’s tenacity on the tennis courts that earned him the nickname “the crocodile,’ the iconic Lacoste logo is immediately recognizable as a sign of good taste.

The brand’s crocodile-embroidered polo shirts have become so popular in fact that a rival company made an anti-preppie version of the garments and was promptly sued by Lacoste.

Fred Perry

Following the success of Lacoste’s preppy athletic wear, British tennis champ Fred Perry decided to make a sports shirt of his own. 

The distinct tennis shirt style has recently popped up in the news after being chosen as the favorite of far-right extremists.

I think that’s a shame because the old-school style is pretty cool. Perhaps it’s time for the preppy movement to find a way to reclaim one of their classic shirts?

Modern Preppy Clothing Brands

Pretty much any preppy clothing brand that originated after the 1970s takes on a different look and feel than the classic brands. There are plenty of newcomers to the “prep” scene looking to make their mark on the preppy aesthetic with unique details, different sales models, and updated looks. 

The following nine brands are the best modern preppy clothes you’ll find today.

Ralph Lauren

There may be no other fashion brand as synonymous with New York City-style as Ralph Lauren. 

Founded in 1967 by its namesake fashion designer, the company now oversees a massive selection of brands catering to different price ranges and styles.

See Also: Clothing Brands Like Ralph Lauren

There’s almost nothing in the preppy style book that’s not offered through one of Ralph Lauren’s brands, making it a one-stop shop for building an entire wardrobe.

J.Crew

Though it was technically founded as far back as 1947, J. Crew didn’t take on its current name until 1983 — the same year that they shifted their attention to a refined but affordable aesthetic that would become almost immediately popular with preppy culture. 

Their collection of well-made basics and essentials with quality materials makes J. Crew a favorite of budget-minded guys who still want to dress preppy.

Vineyard Vines

Immediately identifiable by their distinctive pink whale logo, Vineyard Vines has become the high-end retailer of choice for a modern preppy style. 

Shep and Ian Murray, the brand’s founders, began by selling bespoke neckties out of the back of their Jeep in Martha’s Vineyard. There’s still a little bit of that iconoclastic look and feel in everything the brothers make. 

Their online store is an excellent place to shop for summertime essentials in particular.

Bonobos

Since its birth in 2007, Bonobos has been revolutionizing how guys shop for high-quality wardrobe pieces in both casual and preppy styles.

That’s because they were part of the first wave of online-only men’s clothing brands, effectively cutting out the middleman and seriously reducing costs on top-quality clothing.

While now they’re a subsidiary of Walmart and have some brick-and-mortar retail locations, the impeccable designs on their khakis, button-downs, polos, and suits are well worth checking out.

Faherty

The New York Times said it best when describing Faherty Brand’s style– it reminds them of “Surf hippies.”

The laid-back clothing doesn’t go nearly as far as dedicated surf brands, though; it’s more like a beach-centric version of the preppy aesthetic than a full-blown flower child brand. 

Since its debut in 2013, the brand has continued to expand its offerings past their initially successful board shorts. Be sure to check out their henleys as a classy base layer option.

Rowing Blazers

One of the newest preppy clothing brands to hit the scene, Rowing Blazers has managed to develop a serious cult following in the few years since coming onto the scene in 2017.

By combining a keen understanding of streetwear style with the classic cuts of traditional preppy clothes, they’re putting a whole new spin on what it means to dress like a preppy in 2023. And yes — their blazers are crazy cool. 

Preppy Shoe Brands

And to complete any preppy look, you’ll need to finish it off with a pair of shoes. Here are the best preppy shoe brands, covering a wide range of prices and styles.

Sperry

Sperry’s original top-siders are the boat shoe — the one that defined the market even as it created it.

It all came about because of founder Paul A. Sperry’s experience falling over the side of a boat after his shoes slipped on the wet deck. And no joke, he designed the shoe’s grippy traction-enhancing grooves after watching his cocker spaniel run down an icy hill without sliding or slipping.

If you want preppy footwear, Sperry should be your first stop.

G.H. Bass & Co

Founded by George Henry Bass in 1876, G.H. Bass & Co lays claim to being the oldest producer of top-quality men’s footwear on this list.

Their Weejuns and penny loafers are the stuff of legend and have been favorites of Ivy League students and professors for decades.

If you’re looking for the dressier side of preppy shoes, G.H. Bass is the way to go.

Beckett Simonon

As is the trend in men’s clothing these days, cutting out the middleman does just as much for the quality to price ratio of shoes as it does for clothes.

Beckett Simonon is one of the first and best footwear companies to offer direct-to-consumer pricing through their online-only shop, and their lovingly handmade boots and shoes are an absolute steal for the price.

While Beckett Simonon doesn’t only make preppy shoes, they do offer affordable, high quality versions of preppy footwear staples like penny loafers and Oxfords.

Frequently Asked Questions About the Preppy Aesthetic

And to wrap things up here, let’s take a look at the questions we’ve heard guys asking about preppy clothing brands and the whole preppy aesthetic.

What Do Preppy Men Wear?

There is no one size fits all approach to dressing preppy. But think of it this way: Take any standard outfit you might wear, make sure each piece’s cut and fit are slimmer and more form-fitting, then add in classy shoes and/or outerwear.

For example, trade jeans for chinos, then add a contrasting color of polo and boat shoes without socks. Or dress up form-fitting slacks with a blazer, but wear a t-shirt instead of a button-down underneath.

What Clothes Are Considered Preppy?

The definition of what makes “preppy” clothing has changed over the last few decades, and it continues to evolve.

We’d recommend taking another look through the brands above to get a better feel for the style, rather than trying to stick to specific rules of what is preppy and what’s not.

Is Preppy Style Casual?

Preppy style tends to fall somewhere between casual and classy, with simple clothes that pay close attention to details, materials, and colors.

Do Preppy Guys Wear Black?

Black is not a very common clothing color for dressing in a preppy style. The preppy aesthetic may seem dressy, but it’s not usually formal (e.g., business formal or black tie).

So, preppy outfits typically feature non-black colors and favor brown or navy over black.

When Was the Preppy Look Popular?

The OG preppy look became popular starting way back in the early 1900s, gained even more popularity by the ’40s and ’50s, and continues to experience resurgences in popularity every 20 to 30 years.

At this point, preppy style has transcended the usual cycles of fashion and is a good standby choice for your wardrobe.

Which Brands Will You Wear?

As you can see, there are several great brands that offer clothing that’s perfect for the preppy aesthetic. The question is, which brands will you wear?

Questions? Comments? Leave them below!