One of the most famous dressing styles, The "Preppy" look came from a sincere effort to capture the "American Ivy League" vibe in the 1900s. Later on, IVY famously went global, gaining notable traction after being adopted by young rebellious Japanese men railing against the norms of Japan's unspoken adherence to stuffy dress codes.

Later still, the boomerang swung back to America. And the prep look has enjoyed a resurgence in every decade, with J. Crew becoming the definitive preppy brand in the United States, along with brands like Polo and Tommy Hilfiger.

But what exactly is preppy?

Remember "The Hilfigers"?

Really, you can't go wrong dressing like a preppy. It can include a blend of:

  • Sporty elements (think rugby shirts, varsity patches, tennis, and boat shoes)
  • Formal pieces (blazers, khakis, pants with pleats, crisp denim.)
  • Rugged pieces: (LL Bean type gear)
  • Layering
  • Bright colors mixed with traditional neutrals

Aspirational preppy looks conjure up fantasies of sails in sailboats. Drives in Saab convertibles. Lounging in Jeep Wagoneers. Eating clams upon Pendleton blankets while fireworks light up some coastal enclave. Or some variation of all that which includes tennis courts or polo fields.

How Has The Preppy Look Changed?

These days, styles are more interwoven as creative peeps like you blur traditional boundaries. High-performance materials have worked their way into everyday wear. Preppy isn't as overtly aspirational as it used to be. It's more of a mood, not an in-your-face, Bradley-Cooper-in-Wedding-Crashers affair. Let's call this the "new preppie" style.

Hallmarks of the New Preppy Style

  1. Mixes in high-tech outerwear elements
  2. You can wear black and be preppy, too
  3. Embraces and mixes heritage styles

J. Crew and Preppy

Dogs and Fashion insiders are bullish on J. Crew "righting the ship"

A modern-day juggernaut of Prep, J. Crew is an American retail company that was founded in 1983 by Emily Scott and her husband, Arthur Cinader. The company started as catalog-based, offering classic, preppy apparel and accessories for men, women, and children. In 1989, J. Crew opened its first retail store in New York City, and expanded to operate hundreds of stores across the United States.

In recent years, J. Crew has faced financial difficulties and has undergone several changes in ownership and management. Along the way, their stuff became, well, kind of uncool.

Although J. Crew has fallen out of favor in recent years, it is attempting a renaissance, with Libby Wadle, who previously led Madewell, taking over as CEO. The brand has also brought on Brendon Babenzien, a former Supreme executive and Noah founder, to work on men's apparel, giving the brand a much-needed creative infusion that has many menswear aficionados cautiously bullish about a possible return to glory for the brand.

Brands that are similar to J. Crew, but better.

Let's talk about some non- J. Crew brands we recommend. While these awesome brands might not be "true prep", they have elements of the newer preppy style. Look through what they have to offer, and try them if you want to do the preppy thing, but with a twist.

Although much of this stuff might give you sticker shock compared to J. Crew prices, the "fast fashion" aspect of J. Crew is what sank the brand to begin with. With these brands, you'll get the highest quality for your elevated preppy look.

Engineered Garments.

Preppy for The Adventurous.

Engineered Garments

📸Engineered Garments

This USA-made brand excels if you want to pull off the preppy look, with a twist. Shirts of unique proportions, innovative vests, and versatile coats. Engineered Garments often try new things, for your enjoyment.

If you want to dress prep and look creative Engineered Garments is the brand for you. Start layering up and get your prep on.

Engineered Garments - Classic Shirt - Cotton Paisley Print - OR021
Classic Shirt - Cotton Paisley Print オープンカラーに、裾がスクエアにカットされたボックス型シルエット、両胸のフラップポケットが特徴的なデザインのクラシックシャツ。ドレスシャツとは異なる力の抜けたカジュアルなデザインで、気軽かつデイリーに着用できるユーティリティ性の高いアイテムです。ネイビーベースのペイズリー柄が目を引く個性的な一着となっています。 商品の詳細 原産国: アメリカ カラー: ネイビー サイズ: S, M 素材: 綿100% モデル着用サイズ: - (-cm -kg) ※タンブラー乾燥はお止めください。 ※生地の特性上色落ち致します。お洗濯は単品でお取り扱いください。 ※お洗濯には中
Engineered Garments SAS Jacket Red Fake Poly Fake Melton
You can not get more classic EG than this. RED MELTON OUTERWEAR. This is a throwback to 2013 when Fong was wearing Alden Indy boots, tight Unis pants and Band of Outsiders oxfords. The same could actually be said for Jonathan. So when we first saw this we knew it was an immediate cop. An ode to an era of EG that forever changed menswear. This piece is built off nostalgia. Hood with throat latch Button flap chest pockets Button flap hip pockets with side hand warmer pockets Rear button flap pockets Quilted lining 87% polyester 10% rayon 3% spandex Made in USA Model is 6′1
Engineered Garments BA Shirt Jacket Green Cotton Heavy Twill Plaid
This is the piece of the season from EG. We’re hitting high on the MWW richter scale. I’m talking 3.6 at least. Meaning I’m wearing this bad boy at minimum three times a week with an occasional fourth when I’m feeling frisky. Between the fabric, colour and fit this one has sell out written all over it. Oh and don’t forget, like every EG piece we bring in, this banger has MULTIPLE pockets! Open collar Slotted patch chest pocket Button flap chest & hip pockets 100% cotton Made in USA Model is 6’0” (183cm) tall, weighs 160lbs (73kg) and is wearing a size M

Stone Island.

Modernized Preppy.

Stone Island

📸Stone Island

Stone Island has gained a lot of attention in recent years. For good reason. What sets it apart is its technical properties and proprietary dyes and fabrics. Stone Island gives you a unique edge in the world of prep, by not being overtly prep. If that makes sense.

Try a pair of Stone Island cargo pants, a corduroy shirt, or a next-level jacket. Layer your Stone Island over your rugby shirts and khakis to get a sporty preppy style that's all your own.

115WN Brushed Cotton Canvas Overshirt - Fuschia
432X1 MARINA Ripstop Prismatico C/CAPP Reversible Jacket - Sky Blue
64151 Cotton Fleece Garment Dyed Hooded Sweatshirt - Sienna

The Row.

For The Preppy who wants to wear black.

The Row

📸 The Row

You want preppy, but you love the color black. Try The Row. Sure, this brand will strain your wallet like a pocketful of granite. But The Row is tops if you want to rock the city-preppy look. You are confident, you are going places, and you are the preppy in black.


For Southwestern Preppy Vibes


📸 Mr. Porter

Achieve the coveted "Southwestern Preppy" look with RRL. While Polo and many of its subbrands have gone out in and out of favor in recent years, RRL has retained its swagger.

RRL Logo Jersey T-Shirt - Navy
This Logo Tee from Double RL is constructed from a super soft, lightweight garment-dyed cotton jersey, achieving the aged ‘lived-in’ feel reminiscent of your favorite vintage tee. Lightweight, garment-dyed cotton jersey Printed “RRL” ranch logo Straight hem and crewneck Slim fit that runs true to size We recommend taki
Farrell Workshirt - Pink Multi
The Farrell Workshirt from Double RL is made from medium-weight cotton that’s woven with a pattern inspired by a 19th-century homespun plaid. It has a perfectly relaxed fit that runs true to size and comes with muslin reinforcements at the interior, authentic runoff chainstitch construction at the side seams, and has b
Indigo Oxford Shirt - Rinse Blue
This Oxford Shirt from Double RL is made from lightweight cotton twill that’s been dyed with true indigo and washed for extra softness. It’s detailed with an Oxford collar, a single chest pocket, and finished with a slimmer cut than other RRL styles, so we recommend taking one size up for a more relaxed fit. Lightweig
Lynton Moto Jacket - Black Over Brown
The Lynton Moto Jacket from Double RL is crafted from full-grain cowhide that’s been finished with a black-over-brown hue and carefully distressed to allow it to continue to uniquely age with wear. Finished with a yarn-dyed checked twill at the interior for added comfort, moleskin-lined hand-warmer pockets, and custom

Beams +.

Possibly the Best Neo-Preppy Brand in the World?

Beams Plus

📸 Peggs & Sons

Beams Plus has the preppy game on lockdown. Think Japanese design sensibilities fused with good old preppy style. Focusing on the classics, Beams always delivers. If you want a brand that will give you quality and style, keep your eyes open for Beam's offerings.

Beams Plus Cardigan Aran Patchwork Multi
Oh yes. My first thoughts. Seriously, literally what came to my mind when I saw this. I could even replace the oh yes with an oh my. That’s how incredible this piece is. Look at this colour combo of patchwork. Some could call it brilliant. We call it multi. Saddle shoulders Button closure Patch hip pockets Ribbed collar, cuffs & hem 100% nylon Model is 5’8” (172cm) tall, weighs 130lbs (59kg) and is wearing a size S
Beams Plus Bal Collar Coat Harris Tweed Gun Club
Have you ever wanted to be part of a gun club but didn’t want to buy a gun? Well...if you get this coat you’re half way there, albeit I would still like to get a gun. Harris Tweed wool Concealed button closure Adjustable button tab cuffs Button welt pockets Interior pockets Rear single vent with button closure Fully lined 100% wool outer, 100% cotton body lining, 100% cupro sleeve lining Model is 5’8” (172cm) tall, weighs 130lbs (59kg) and is wearing a size S
Beams Plus Check Vest Mohair Grey
This is on me. I specifically remember saying this is going to be my jam for FW23. There are two things that i have straight love for in life. Vest and mohair. What happens if they come together? Well then we know what happens. We are 100% bringing it in. Case and point. To quote the immortal Dylan, ‘I spit hot fiya’. V-neck Ribbed neck, armholes & hem 40% nylon 32% mohair 28% wool Model is 5’8” (172cm) tall, weighs 130lbs (59kg) and is wearing a size S
Beams Plus B.D. Classic Fit American Oxford Blue
Tried. Tested. And true. I literally could say this about most Beams Plus pieces but for the oxford, we know what’s up. This is the classic of the classic and not many people do it better. Between fabric, fit and feel this is what you’re going to want to live in on casual Fridays. Hey now! Button down collar Chest pocket Curved hem Signature

CDG Play.

A Preppy Brand to Get Fully Uniformed Out In

CDG Play

📸 CDG Play

An alternative to preppy clothing brands like Ralph Lauren, COMME des GARÇONS Play rocks. With a focus on classic, timeless pieces, CDG Play is the perfect brand to get uniformed out in. When you rock the peeping heart you'll stand out in all the right ways.


A Preppy Brand For Those Who Love Cashmere



Cashmere is still one of the loveliest things you can wear. And one of the loveliest brands making cashmere things is Frenckenburger, a Swiss brand with a flair for the ultra-comfy. This stuff is maximal-comfy without veering into the "loungewear pajama" departments. When you're upgrading your preppy style to luxury preppy style, choose Freckenburger.

4S Designs.

Preppy for the Next Level


📸4s Designs

This brand is "next level" preppy. 4S uses Euro-quality materials and good old American construction with a new vision of prep. Great for people who want to continue to push the boundaries of what preppy clothing can be. Keep an eye on this brand!

J.W. Anderson.

Colorful Elevated Preppy.

J.W. Anderson

📸J.W. Anderson

Anderson is the Creative Director at Loewe, which should tell you something. He got there on the strength of his eponymous brand, which is innovative and fresh to this day. His designs are full of color and feature Nautical motifs and 90's preppy influences. You know, like Tommy Hilfiger before it became outlet fodder.

Have Fun with Your Preppy Self

Maybe these brands aren't all Ivy, all the time, but dig through their collections and develop your own preppy style! And most of all, have fun. ✌🏻

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