Picture this: you’re standing in front of your closet, feeling bored with your wardrobe. You’re ready to change and elevate your style but unsure where to start. You know you want to achieve the preppy aesthetic, but trying to master this classic style seems overwhelming. With their various colors, patterns, and textures, preppy shirts can help you achieve your goals and make the transition to a new style more manageable. 

This blog will help you understand how to select the best preppy shirts for your journey to master the preppy aesthetic and elevate your personal style.  WhatColors' AI personal color analysis app will help you get there faster by providing personalized insights on the colors that will look best on you.

Table of Contents

• What Defines a Preppy Shirt?

• 6 Key Types of Preppy Shirts

• How to Style Preppy Shirts

• 28 Must-Know Preppy Shirt Brands for the Perfect Wardrobe

• 7 Must-Have Preppy Shirt Accessories

• Try AI Personal Color Analysis For Free Today

What Defines a Preppy Shirt?

The quintessential preppy shirt excels in three key areas

• Fabric

• Collar

• Pattern
  
  

Preppy shirts are usually made from cotton or some variation thereof. They are not the crisp poplin fabrics that dominate dress shirts. Instead, you’ll want to look for soft, casual materials with some weight. Think of brushed cotton twill or even flannel for colder months. These materials will help create a warm, inviting aesthetic that is perfect for your next outing.

Collar Style

Examine the collar. While your typical dress shirt features a stiff, structured collar, the preppy version has a soft roll. This type of collar's more casual appearance is better suited for a life of leisure, precisely what you want your preppy shirt to convey.

There are patterns. Preppy shirts often reference heritage sports that have stood the test of time. These include:

• Stripes

• Checks

• Other timeless motifs evoke images of sailing, golf, and other activities enjoyed by the elite

Solid color versions in rich hues also fit the bill.

The History and Cultural Significance of Preppy Shirts

The term preppy derives its name from the preparatory schools that the elite attended before enrolling in Ivy League universities. The style became popular in the early 1900s, conjuring images of:

• Privilege

• Old money

While the style is still associated with the upper class, anyone can enjoy it regardless of background today.

Shirts that embody the preppy aesthetic can elevate your style by adding a touch of class to any outfit. They are accommodating for smart casual and business casual settings where you want to convey that you mean business but also have a life outside of work that involves:

• Fun

• Leisure

• Plenty of socializing

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6 Key Types of Preppy Shirts

Oxford Cloth Button Down

Perhaps the definitive preppy shirt is the Oxford cloth button-down, an OCBD. The OCBD is effectively the very first iteration of what we know as the polo shirt. It looks nothing like today's piqué cotton polo shirts—you must swing back to late 19th-century India to find its genesis. 

There, British Army officers found that their regular issued shirts could have been better for playing polo when off-duty. Since the collar points would flap in their faces, they came up with the idea of buttoning them down. It wasn’t until an American businessman named John E. Brooks—the grandson of Henry Sands Brooks, who founded the Brooks Brothers company in 1818—noticed them on a business trip to the UK that the OCBD gained traction. 

Hollywood Influence

Brooks noticed these new shirts being worn by society’s movers and shakers and immediately began to produce his very own version when he returned to the States. Launched in 1896, the button-down was an instant hit, helped in no small part by Hollywood’s uptake of the shirt, with:

• Messrs

• Gable

• Astaire

• Bogart

• Grant 

• Later, Paul Newman 

• All proponents of this new casual design before it gained traction in the Jazz movement and on Ivy League campuses

Oxford Cloth

The button-down bit speaks for itself, but the Oxford bit refers to the cloth, which has a weave similar to plain canvas, except that several yarns are woven in strands together rather than individually. This gives it a very soft and comfortable handle. 

Today, the OCBD is often cut from brushed cotton or wool flannel, which gives it a slight nap that feels super soft and warm. Construction-wise, the OCBD should have a soft collar roll and will often come with a box pleat in the back; it’s not a particularly fitted design.

1. Flannel Shirt

From the unforgiving valleys of Wales to the 90s grunge movement via the Industrial Revolution and the Great Depression, the flannel shirt symbolizes rugged, enduring masculinity and a nonconformity motif. 

Today, its meaning is benign in comparison, but it’s no less an essential part of a stylish modern wardrobe, especially in the fall and winter months when it comes into its own. Flannel is a relatively loose term, which is why you can find flannel shirts made from:

• Cotton

• Wool 

• Synthetic fiber

Flannel Fabric

It describes a reasonably heavy, soft material brushed on one or both sides to create an ever-so-slightly furry nap. It’s believed to have originated in Wales in the 17th century when it was usually made from coarse wool and worn by farmers who needed something warm and comfortable to brave the weather in the valleys. 

These days, 100% cotton tends to be the fiber of choice, although it can be blended with silk or man-made materials, too. Heavier flannel, anything around 10oz and upwards, is hardy workwear, probably with some Americana heritage.

Flannel Details

Look for an almost blanket-y feel (not fleece) and flat-felled seams, where the edges are rolled back and stitched on the underside of the shirt.

2. Striped Shirt

In the very early days of preppy origins, British university rowing crews used stripes to differentiate themselves from one another. Various colors and thicknesses of stripes were widely adopted on blazers, and this sporty trend spilled over into shirts. 

Today, as then, a vertical striped shirt still has an inherent sportiness and is an acceptable way to introduce pattern to your look. Preppy styles tend to have thick stripes rather than pinstripes, which are more associated with the city, while horizontal motifs reference vintage rugby shirts.

3. Block-Colour Shirt

Primary colors have been a preppy statement since the 1950s when Ivy League students wore them to distinguish themselves from the boring white and pale blue work shirts worn by their fathers. Pastel tones are another hallmark of the 2024 preppy aesthetic, so ensure you’ve got a full spectrum of tones in your wardrobe. 

Polo Ralph Lauren has, over the years, produced shirts in every tone under the sun and is always a great place to stock up on these classic preppy garments.

4. Checked Shirt

Check shirts, especially Madras checks, have always been a popular preppy look and offer a helpful way to break up your outfit with patterns. Madras cotton comes from the Chennai region of India, down on the southeastern tip of the country. In the mid-19th century, British and French textile manufacturers were tripping over to acquire it as it was cheaper than European cotton.

Madras History

This led to the East India Trading Company incentivising Indian fabric makers. If they moved to Chennai and focused all their efforts on Madras production, they would benefit from a 30-year tax exemption. Madras caught on in the US when the Collegiate School of New Haven, Connecticut, was pitching for financial donors and met a British Governor called Elihu Yale, who had made a fortune while in Chennai. 

He donated, among other things, large amounts of Madras cloth. In a show of their gratitude, they renamed the institution Yale University. Madras fabric couldn’t be any more preppy if it tried.

5. Polo Shirts

Polo shirts, or golf or tennis shirts, are a well-known staple in prep style. They are casual and soft, with a collar, placket, and usually two or three buttons. A breast pocket is often featured. Made from knitted piqué cotton, they can also be found in:

• Silk

• Merino wool

• Various synthetic materials

Polo Versatility

Polo shirts are often worn with shorts or trousers but can also be paired with a blazer or sports jacket.

6. Seersucker Shirt

A prep wardrobe staple, seersucker shirts are the ideal go-to item for a novel and refreshing look. Made from puckered cotton, seersucker is a light and breathable material ideal for:

• Spring 

• Summer

Of significant note is that seersucker shirts should be tucked in to preserve the formal, preppy look.

How to Style Preppy Shirts

Styling preppy shirts is all about achieving a polished yet laid-back vibe. Pair a button-down shirt with tailored trousers or chinos for a classic preppy ensemble, finished with loafers or boat shoes. 

Layering is essential, so don't be afraid to add a cable-knit sweater or a lightweight blazer for extra warmth and style. Experiment with color-blocking and mixing patterns to add visual interest to your look while staying true to the preppy aesthetic.

Level Up Your Style With Seasonal Styling Tips 

When styling preppy shirts, remember to consider the weather. Don’t be afraid to layer your polo underneath a cozy sweater or a preppy cardigan in the fall. You can even let the polo collar peek out for added visual interest. Add a classic wool coat for a polished, preppy look as the temperatures drop. 

Come spring, you can enjoy the lighter fabrics and bright colors of polos and other preppy shirts. These styles look great on their own but pair nicely with classic blazers. For warmth, layer a lightweight cardigan over your preppy shirt for your transitional weather outfits.

WhatColors’ Color Analysis

WhatColors helps you find what colors to wear based on your skin tone. Thanks to our patented color match technology, you can get your season based on your skin tone. Get the perfect colors based on your season. Avoid colors that are a definite no. Based on your skin, eye, and hair color, find the perfect nail colors with our WhatColors nail color generator. 

Get your color analysis done within 60 seconds with WhatColors’ AI personal color analysis app. Download our app for free today on the App Store or Google Play store.

28 Must-Know Preppy Shirt Brands for the Perfect Wardrobe

1. Collars & Co.

Elevate your wardrobe with preppy shirts from Collars & Co. Born out of a desire to provide a more comfortable alternative to wearing dress shirts under sweaters and jackets, Collars & Co. set out on a year-long journey to create the perfect buttery-soft polo with a standard English spread collar. The result? A luxurious yet practical garment that combines comfort with refined style.

2. Neem London

Neem London's overshirt is a testament to sustainability and style. Crafted from 100% recycled cotton, it features a lightweight Zephyr weave for year-round comfort. With two side welted pockets and an elegant Prince of Wales check pattern, it's perfect as a:

• Jacket

• Shirt

• Layering piece

Plus, Neem offers a buy-back program promoting circular fashion.

3. Velasca

Embrace timeless Italian craftsmanship with Velasca's range of premium shirts. Founded in 2013 by Enrico and Jacopo, Velasca began with a mission to create excellent quality men’s shoes at a fair price by selling directly to customers. 

Since then, Velasca has expanded its product range to include apparel, maintaining its commitment to delivering freedom and beauty through artfully crafted items.

4. Private White V.C.

Discover the epitome of British craftsmanship with Private White V.C.'s collection of preppy shirts. Established in Manchester in 1853, Private White V.C. has a rich heritage of outfitting kings, queens, presidents, and Hollywood icons with impeccably crafted garments.

With a commitment to quality and tradition, Private White V.C. continues to produce shirts that embody:

• Timeless elegance 

• Sophistication

5. Luca Faloni

Founded with a passion for the Italian style in men's wear, Luca Faloni selects only the finest materials from prestigious Italian producers to create shirts of:

• Unparalleled quality 

• Craftsmanship

Luca Faloni's shirts are designed to withstand the test of time, using materials ranging from pure cashmere and silk-cashmere to linen and brushed cotton.

6. Foret

Embrace the beauty of nature with Foret's collection of preppy shirts. Founded in 2014 with a vision to recapture the sense of the great outdoors, Foret offers high-quality, timeless garments that blur the line between outdoor clothing and casual staples. 

Made from sustainable fabrics and designed for versatility, Foret's shirts are perfect for both the wilderness and the office.

7. Wax London

Infuse your wardrobe with London cool with Wax London's range of preppy shirts. Founded in 2015 by three friends with a passion for dressing well, Wax London combines British style with affordability to create garments that are both:

• Stylish 

• Accessible

From classic striped shirts to casual tees, Wax London offers a diverse range of preppy options for the modern gentleman.

8. Closed

Discover the perfect blend of French imagination, Italian craftsmanship, and German tradition with Closed's preppy shirts. With a focus on quality and attention to detail, Closed's shirts are made to last, using only the following:

• Finest materials 

• Production techniques

From denim to cotton, Closed's shirts exude European heritage and timeless style.

9. Pini Parma

Experience the elegance of Italian style with Pini Parma's collection of preppy shirts. Handcrafted by highly experienced Italian craftsmen, these shirts combine traditional manufacturing techniques with modern design sensibilities. Made from high-quality materials across Italy, they offer a perfect balance of luxury and versatility.

10. Mackintosh

Elevate your outerwear game with Mackintosh's collection of preppy shirts. Established in 1824, Mackintosh is one of the world’s most influential coat makers, renowned for its craftsmanship and expertise in rubberized fabric.

With a focus on quality and innovation, Mackintosh's shirts offer style and functionality for the discerning gentleman.

11. ASKET

ASKET puts sustainability at the forefront of every decision it makes and is incredibly transparent with its:

• Production 

• Pricing processes

It’s a welcome breath of fresh air in an industry dominated by polluting fast fashion brands and opaque luxury price tags. Specialising in everyday staples, the button-down is vital to the Scandinavian brand’s collections.

OCBD Options

From brushed mid-weight 100% organic cotton Oxford cloth milled in Portugal, ASKET’s OCBDs are an industry benchmark. Also, look at the flannel options, cut from a soft, brushed, custom-developed Italian twill made from 100% organic cotton.

12. Alex Mill

New York label Alex Mill was founded by its namesake in 2012 to create the perfect shirt. The brand’s no-fuss approach to making the best possible versions of menswear staples is a breath of fresh air, elevating traditional workwear pieces into something extraordinary.

Its button-downs are made in crisp Portuguese cotton, corduroy, and poplin, with chic stripes and bold colours playing a pivotal role.

13. Arket

You tend to know what you’ll get with Arket: excellent wardrobe essentials crafted from great organic fabrics. So it is with its Oxford shirt, constructed using 100% soft organic cotton and available in six different colorways. At $69/£55 a pop, you can’t argue with Arket’s preppy proposition.

14. Adsum NYC

Founded in Brooklyn in 2015, Adsum NYC has developed a cult following for its high-quality staples inspired by the cities and countryside of the American Northeast. Naturally, the brand has put a contemporary spin on classic flannel shirting by using bright, vibrant plaid patterns for its two-button work shirts. 

Typically constructed from heavy brush 265 GSM custom flannel, the shirts feel incredibly soft and are robust to boot—perfect for wearing with:

• Selvedge denim

• Chinos

• Loungewear

15. Brooks Brothers

The original and best Brooks Brothers’ button-down shirts represent excellent value and give you that heritage cachet as the original purveyors of the style. 

Being the archetypical preppy clothing brand, Brooks has a fantastic assortment of button-down shirts. They have slim and regular fits in classic Oxford cloth and several check options in super-soft flannel, perfect for more outdoorsy looks.

16. Brunello Cucinelli

At the top end of the pricing spectrum is Brunello Cucinelli, whose mastery of delicate fabrics extends to his luxury shirt offering. Buttery-soft materials are the DNA of the Italian designer. So it comes as no surprise to find that Cucinelli presents a button-down collection featuring Oxford cloth blended with lyocell, as well as:

• Pure cotton flannel

• Poplin 

• Twill fabrics

Cut in a slim fit, they are easy to style with contemporary smart casual wardrobes – if you’ve got the wallet.

17. Club Monaco

Since its launch, Club Monaco has nailed that smart, sophisticated Euro-traveller aesthetic. It focuses on elevated staples and slim silhouettes to create a well-rounded, softly tailored look that appears more expensive than it is. 

Its button-down shirts are constructed from Oxford cotton cloth sourced from sustainable farms and offer excellent value for money.

18. Drake’s

On its OCBD, Drake says it best, “With a regular silhouette, floating interlinings, single-needle construction, and perhaps most importantly an elegant rolling collar, it’s a shirt for all occasions.” If you want a perfectly constructed, elevated version of a button-down or flannel shirt, Drake’s is peerless in choice and style.

19. Filson

Filson is one of those iconic brands that has left an indelible mark on the history of American workwear. Founded in Seattle in 1897, it rode the rush of gold prospectors heading north in the Klondike Gold Rush, kitting them out with the warm, rugged kit needed for the bracing elements. 

Then and now, heavy flannel shirts in plaid designs are Filson’s hero product. So, if you’re hunting for outdoorsy, hard-wearing flannel, the search stops here.

20. GANT

GANT’s authority as an all-American brand is second to none and should be the first port of call for those with a modern preppy leaning. Offering an abundance of excellent OCBD styles, including stunning stripe and plaid options, the shirts feature a beautiful soft-roll collar.

With over 150 styles to choose from and in many fabrics, including brushed cotton, twill, and corduroy, we wouldn't blame you if you didn’t look elsewhere.

21. Hartford

As English as it sounds, Hartford is a French brand. Founded in Paris in 1979, Hartford specializes in traditional casual silhouettes in beautiful natural fibers, particularly flannel. One of the cornerstones of its seasonal fall/winter collections, the label produces a vast number of flannel shirt styles—including:

• Plaids

• Gingham

• Brushed denim options

22. Husbands

Sophisticated Parisian outfit Husbands might only create a small number of Oxford button-downs, but each one is an intelligent iteration of the classic. Designed to be more formal than the traditional preppy style, Husbands’ OCBDs feature a stiffer and more oversized collar than normal, making them more suitable for pairing with a tie. 

Using both Turkish poplin and Japanese Oxford cloth, this small but beautifully formed curation of OCBDs makes an excellent addition to a modern business casual wardrobe.

23.J.Crew

The beauty of J.Crew’s website is that you can shop for shirts by fabric, making finding a suitable OCBD easy. Choose between broken-in Oxford cloth, brushed twill, corduroy, and midweight flannel, then explore the many:

• Color

• Pattern

• Fit options

24. Oliver Spencer

Oliver Spencer’s unique take on relaxed tailoring sees the British designer release a number of button-down and flannel shirt options each season – always in super-soft organic cotton fabrics, from brushed cotton to textural twills and corduroy. 

His signature button-down goes by the name of the Brook shirt and features a distinct soft-rolled collar.

25. Portuguese Flannel

Fun fact: Portugal is Europe’s biggest producer and exporter of fine flannel fabric. So when a company named Portuguese Flannel comes along, it might be a good idea to check out its range of shirts. Predictably, this relatively small fourth-generation, family-run outfit based in Porto produces excellent preppy flannel shirts. 

Each of its lightweight shirts is manufactured close to home in the country's north, using predominantly organic and recyclable cotton fibers.

26. Ralph Lauren

Oxford button-downs are an integral element of Ralph Lauren’s timeless American preppy aesthetic, so the legendary designer always delivers the goods with his core collection of OCBDs. 

Via his Polo label, available in almost every color you can think of, there is a huge amount of choice, from cotton poplin fabrics to twills and brushed styles and various fits. 

• Solid

• Classic

• Modern Americana

27. The Real McCoy’s

A Japanese vintage specialist, The Real McCoy’s reproduces the best menswear silhouettes from the 1930s onwards. Its flannel shirts, produced under its 8-Hour Union Label in classic plaid and houndstooth patterns, are always highlighted. 

Think heavyweight flannel with rolled stitches, referencing the traditional workwear shirts of the 1950s American laborer. If you have a penchant for Americana, you’ll love its flannel options.

28. Uniqlo

The Japanese retailer of everyday essentials would be remiss if it didn’t have an eclectic range of preppy shirts, but of course, it does, and at a fantastic price point, too. 

For a fraction under $40/£30, Uniqlo offers slim and regular-fit Oxford cloth and cotton flannel shirts in an array of easy-to-style plain designs and plaid and stripe options.

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7 Must-Have Preppy Shirt Accessories

Accompanying your preppy style with colorful and bold accessories is critical. While conventional collegiate style ties, such as the one below, will almost always do the trick, there are alternative ways to spice up your ensembles with patterns that will have you standing out in a positive, counter-culture manner.

1. Plaid / Madras Ties

Madras ties, popularized by prepsters in the northeast, are characterized by plaid patterns on cotton fabric. While there is a class of Madras products that refers to patchwork, we are referring to woven plaid designs. A Madras Plaid Tie can instantly elevate your preppy outfit and have you stand out!

2. Animal Print Silk Ties

In line with injecting color into your ensembles, these unique printed silk ties often feature repeating animal motifs, such as sea life, birds, or chicks. Similar silk ties that feature repeating motif prints include lifestyle ties (e.g. golf balls, tennis racquets, palm trees). 

These unique neckties are instant conversation starters, given that they appear as a splash of colors from afar. Still, they often reveal something about the wearer’s interests/hobbies upon closer inspection.

3. Knit Ties

Knit ties have enjoyed a renaissance in recent years and are ideal for adding textural variation to your attire and can elevate your preppy look! They can be used to dress up a less formal look or to dress down a more formal look.

4. Pocket Squares

If you are looking to provide your attire with that final complementary piece that will have you looking like Justin Timberlake’s right-hand man, and the ideally dressed prepster, a paisley or floral pocket square will undoubtedly add to your overall look.

5. Anchor Bracelets

Anchor bracelets sound exactly like bracelets made from various fabrics and materials, usually rope, leather, or sail cloth, and fastened with a small metal or plastic anchor that operates similarly to a hook. 

This jewelry is trendy in prep culture with men and women and is about as nautical as possible.

Color Palette

While these patterns can be found in solid blacks and grays, the bright colors that are most popular are:

• Blues

• Greens

• Pinks

6. Belts

Colorful belts with motifs and stripes are integral to a preppy wardrobe. Often combined with brown leather and a brass buckle, these more or less flexible cloth belts are combined with:

• Chinos

• Madras

• Seersucker pants to create a bold look.
  
  
  

D-ring or Ribbon Belts Traditionally called Ribbon Belts, D-ring belts have been around since the mid-1960s, when J.Press introduced them. They provide a casual and fun flair to a normally conservative look. Some say that to wear them, you either need a sense of humor or a small budget since many D-ring belts are reversible, offering two-in-one belts.

7. Preppy Style Knitwear

Argyle Sweaters The argyle sweater is predominantly seen in golf apparel, so it has become ingrained in the prep culture. Since golf has long been a favorite pastime for preppies, Argyle has become a fashionable pattern amongst both men and women. The pattern can be made up of diamonds or lozenges.

Typically, they overlap in a motif, adding a sense of multiple dimensions and texture. In most cases, it’s used as an overlay of intercrossing diagonal lines on solid diamonds.

• Cable-knit sweaters are classic and will never go out of style. Whether made of cotton, wool, or cashmere, with sleeves or without, they are a preppy wardrobe staple. 

• A crew neck is the way to go if you wear bow ties, while ties look great with V-neck sweaters. 

• For a soft, casual outfit, look for a melange two-tone yarn, which lends the sweater a mottled, gentle look.

• Tennis & Cricket Sweaters Tennis or Cricket sweaters are a must-have in a preppy wardrobe.

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Try AI Personal Color Analysis For Free Today

WhatColors helps you find what colors to wear based on your skin tone. Our patented color-match technology lets you get the perfect colors for your season. Avoid colors that are a definite no. Based on your skin, eye, and hair color, find the perfect nail colors with our WhatColors nail color generator. 

Get your color analysis done within 60 seconds with WhatColors’ AI personal color analysis app. Download our app for free today on the App Store or Google Play store.