The 14 Best Preppy Clothing Websites and Brands

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by  Dean Stephens | Last Updated:  Sep 23, 2020

Here’s a question for you.

What’s the first thing that comes to mind when you see the famous Ralph Lauren “polo” logo positioned atop a crisp purple zip knit sweater?

‘Typical rich kid?’

Harsh but we hear where you’re coming from.

‘Painfully common?’

Yeah, it’s getting that way.

All of that aside, for me, Ralph Lauren still screams ‘preppy’. The preppy style is one that is easily identifiable, and understandably so. It’s been around for generations.

While often dismissed as being too traditionalist, we can understand the appeal of the look. It’s clean, colorful, and in a sense, unifying. It reflects the attention to detail that is demanded by the perfectionists of style.

There exists a group of clothing brands that have built reputations on creating garments that are geared toward (or in some cases, helped to create) the preppy trend.

The following, in no particular order, are the top preppy clothing brands (in our opinion) that you should explore if you’re keen on crafting a memorable preppy look.

Fred Perry

As one of the first brands to create a look that fits within the prep aesthetic, Fred Perry not only one of the originals, but also one of the best.

A British staple, the Fred Perry label is well-regarded for its effortlessly cool look. The label continues to lead the way for men that seek out clothes that exude the confidence and dapperness that a true prepster demands.

And when it comes to Fred Perry, you can’t go past their staple polo:

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The preppy look may be classic, but that doesn’t mean it’s not open to re-imagination from time to time.

The French are believers in re-invention and the brand A.P.C. not only combines traditional aspects of the prepster look but introduces other interpretations as well.

Their clothes are more fitted and daring, staying true to the mantra in French style, while proving that preppy clothing can evolve over time and still maintain a distinct look that speaks volumes.


Moreso than any other criteria involved in the definition of what qualities dictate the preppy look, authenticity is an absolute mandate for this aesthetic and only the most respectable brands delve to do it justice.

The Portland-based brand Pendleton has been around for over a century and show no signs of slowing down.

For a true look that effectively captures the prep look down to a T, Pendleton is one brand men can turn to that guarantees a finished product that is well worth the investment.

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Opening Ceremony

Although the preppy look has always been considered a more traditional aesthetic, that doesn’t necessarily mean that it is or has to be bland.

Opening Ceremony is one brand that revels in the conventional while putting their own visual stamp on the preppy look, which has garnered them acclaim within the community for their approach to the style. For the fashion-forward man that lives for mixing it up and going against the grain sartorially, this is a label that gives you more bang for your buck.

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L.L. Bean

For the ultimate in prepster apparel, one need look no further than heavyweight L.L. Bean.

The company is known worldwide for its signature pieces, many of which continue to make a significant impact on the prep aesthetic for men across several generations. The New England-based company draws heavily on American culture and history as inspiration to create their apparel, and that lineage has endeared them to those that look to encapsulate the modern, preppy look that speaks volumes.

For great quality and a reputation that precedes their years of immense efforts, L.L. Beans represents some of the best that can be found on the market today for the preppy man.

Sir Jack’s

sir jack's screenshot 05072017

As one of the most respected gentlemen’s outfitters around, this Boston clothier boasts quality apparel that is specifically for men with discerning tastes, making it a natural fit for men that want a preppy look that exudes great taste.

From men’s apparel all the way down to accessories, there are few brands that deliver across the board like Sir Jack’s.


They’ve studied the style book when it comes to creating great preppy apparel for men and that expertise has led to a huge following worldwide.

Men that want an exceptional fit can turn to Bonobos for clothing that helps every man achieve the perfect fit from head to toe.

J. Crew

By choosing style over substance every time, J. Crew has earned the respect of men worldwide for creating and maintaining a preppy look that is bold and innovative in its appeal.

From their sneakers to their sweaters and even their suits, the J. Crew brand is demonstrative of what the preppy look is all about.

Brooks Brothers

Every man of the preppy persuasion has heard of Brooks Brothers. And every man who wears clothes probably has as well.

Founded in 1818, Brooks Brothers is universally accepted as an iconic innovator of American style.

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As a British label that exudes class and distinction, Burberry puts a contemporary spin on the preppy aesthetic, with several of their pieces now considered classics.

Men that are searching for a look that speaks volumes without saying a word, Burberry is the brand to check out.


How could we leave out ‘the crocodile’?

As one of the leaders of the prep scene, French giant LaCoste has drawn legions of fans to its stable with its traditional, clean, and functional fashion offerings.

We love the classic white Europa when it comes to Lacoste:

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Sperry and boat shoes. They go together like prepsters and uh…boat shoes.

Paying homage to the seaside aesthetic, American clothier Sperry are yet another example of a preppy brand that has remained true to its roots.


Although they create a great line of clothes that include trousers, shirts, and a host of accessories, Barbour’s wax jacket still stands tallest as its crowning jewel.

Add one of these to your wardrobe for ultimate prep versatility.

Ralph Lauren

While it’s arguably slipped into fashion normality in recent years, Ralph Lauren remains the quintessential king of men’s preppy brands on tradition alone.

It’s no secret that the Ralph Lauren empire takes style seriously, and with each successive collection over generations, they have only added to the allure attached to their prepster creations.

There you have it. Are there any more brands you’d include? Chat with us in the comments.

Until then. Game of croquet anyone?

If you’re interested in learning more about the history of the preppy style, give this great guide a read.