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    How to Wear Preppy Men’s Clothes (Comprehensive Preppy Style Guide)
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How to Wear Preppy Men’s Clothes (Comprehensive Preppy Style Guide)

If you’ve been searching for a preppy style guide, you’ve definitely landed on the right page. Today, we go into extensive detail deconstructing the preppy aesthetic. You’ll learn how to wear preppy clothes, how to build a smart wardrobe, and how to genuinely look the part with the right brands. We also feature an array of the best preppy men’s clothes, so stick around.
Preppy Style Guide - Best Preppy Mens Clothes

Preppy Style Guide Table of Contents:

First, What Is Preppy Style?

The term preppy refers to a style of dress, but also evokes an entire lifestyle. In the US, the term comes from the style adopted by private, university-preparatory (prep) schools in New England or Ivy League schools, at least according to dictionary definitions.

That isn’t really fair for a number of reason:

  1. The preppy style of dress is ageless. You can imagine preppy clothing in country clubs, on golf clothes, in yacht clubs, and just for everyday wear for children through grandparents. Elements have been was worn for the last 100 years.
  2. The preppy aesthetic is really classic clothing with a foundation of dressy yet comfortable, quality, practicality, and timeless usefulness.
  3. If you look at the origins of prep fashion, you’ll find that almost everything is based on British middle- to upper-class clothing, especially their university and boarding school lifestyle, with an emphasis on sporting origins.

You can always find the basics of preppy clothing, regardless of current trends. What you may notice is that certain items go from basics to trends periodically, and the entire movement of “preppy” becomes one of the “it” styles every 40-50 years.

Studying the progression of style will also show that the overall look, as well as how certain items are made, has evolved from just prep school fashion to encompass aspects of street fashion.

Today, it’s our goal to give you a primer to help you figure out how to wear the preppy aesthetic.

The Origins of Preppy Fashion

The beginnings of modern preppy are found in the clothing of the 1920’s. Not really the flapper/zoot suit 20’s, but the Ivy League, society foundation.

If you look at pre-World War II Britain, you’ll see pictures of the royal family playing golf wearing caps and Fair Isle sweaters, and women wearing twin sets and pearls. In the US you find pictures of students in letterman jackets, cable knit sweaters, sweater vests, and camel hair “polo” coats.

Related reading: Best Summer Pants for Men

True Prep: It’s a Whole New Old Word

Preppy Style Guide - True Prep by Birnbach
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There was a resurgence of preppy style in the early 1980’s. In fact, Lisa Birnback published a very popular book, The Preppy Handbook, that may have been meant as a satire of the lifestyle, but in reality, became a popular style handbook. 

However, she has since updated the preppy style guide in her new book True Prep: It’s a Whole New Old World (published in 2010), which is readily available. That’s the one we’d recommend if you’re looking for a true deep dive.

How to Wear Preppy Men’s Clothes

The wonderful thing about adopting a preppy style is that you already may have many of the items in your current wardrobe and anything you purchase can be used in a variety of mix and match ways, now and in the future.

The other wonderful aspect of the preppy style is that you can purchase every items discussed here at just about any price point from a variety of manufacturers. Some may specialize in preppy clothing, others just produce practical styles that happen to be part of the preppy world.

Almost everything ranges from vintage, even thrift shop finds, to low-, mid-, and high-priced brands, and even to bespoke clothing. This means that you can put together the same basic an outfit for under a $100 or over $5,000. You may even be able to raid your parent’s or grandparent’s closets for some of the essentials.

One of the keys to preppy style is the ability to layer. This not only allows you to get more looks from a relatively small number of items in a wardrobe, but allows you to dress for changing weather conditions every morning.

Here’s how to get started building preppy outfits.

Preppy Shirts

Like so many other styles, that preppy look starts with the essentials. Think about what you’re going to be wearing every day, and build on top of it.

Here are a few essential shirt choices of the preppy aesthetic:

Polo Shirts

Polo shirts are a great summer top. They were originally worn by polo players and actually had button down collars. (We’ll talk about this more when we get to oxford shirts.)

They all have a knit collar and cuffed sleeve with a 2-3 button placket. And, they come in two weaves: jersey (like your t-shirts) and pique. Pique is a more textured weave and feels thicker than jersey.

Unrecorded Knitted Grey Polo Shirt

Unrecorded Knitted Grey Polo Shirt Shop Now

Unrecorded is an Amsterdam-based clothing brand renowned for its less-is-more approach in menswear design. Clean cut, classic, and polished, this knitted polo shirt by Unrecorded will keep you looking preppy but still comfy. 

Designed with a regular fit from 100% organic cotton and detailed with a buttoned half-placket and mother of pearl buttons all match for a luxurious appeal but still casually cool aesthetic. The rib-knitted hemline and cuffs only add to the preppy twist of the outfit. This knitted polo shirt does have a slightly wider fit. So, when in doubt, size down. 

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Nautica Pique Polo

Preppy Clothes - Nautica Pique Polo
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You can find polos everywhere – from Walmart to high-end manufacturers. Polos first became a popular shirt in the 1920’s. They can be an essential part of even minimalist wardrobes. Nautica, for example, makes pique polos emblematic of the preppy aesthetic without costing a fortune.

Lacoste Pique Polo

Preppy Style - Lacoste Pique Polo
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René Lacoste, a French tennis player, launched one of the very first brands centered around an athlete with his Lacoste polo shirts. He designed his shirts to be breathable, cooler, and have a greater range of motion than traditional tennis clothing. The new style was so popular that is went far beyond mere tennis wear. You can still find the iconic alligator logo on Lacoste shirts.

Ralph Lauren Polo with Contrast Tipped

Preppy Mens Style - Ralph Lauren Contrast Tipped Polo

However, if you are looking for the most iconic modern polo you’ll probably want to start with Ralph Lauren. Since the brand’s launch in 1972 their polo-playing logo has been a sign of preppy quality.

If you are serious about your clothing, or are a hard to fit size, either smaller or larger than standard sizes, you can custom order your Ralph Lauren polos for $168. Luckily there are several other custom t-shirt and polo shirt companies that charge quite a bit less.

Amazon Essentials Jersey Polo

Preppy Look - Amazon Essentials Jersey Polo
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Jersey polos have their fans also, partly because the fabric is sleeker and more finished looking. Every manufacturer will have their own version of jersey polos. Amazon Essentials offers 21 colors and patterns for the price of lunch. 

If you are looking for a slightly better quality jersey polo, you can’t go wrong with Land’s End, LL Bean, Hilfiger, or Nautica.

Henley Shirts

While polos come in long sleeve versions, preppy fans have 2 other options. Both have their beginnings in British sports.

A Henley is a collarless shirt with a rounded neckline, a 3-5” placket with 2-5 buttons. They can be made from either pique or jersey knit.

The original henley was favored by university rowing teams in the nineteenth-century. The name comes from Henley-on-the-Thames, the host of the Royal Regatta. Traditionally, the losing team would give their shirts to the winning team. This is why a buttoned front was important.

Amazon Essentials Slim-fit Henley

Preppy Tops - Amazon Essentials Henley Buy now

Luckily, Henley’s aren’t expensive and most t-shirt manufacturers like Amazon Essentials, Hanes, Carhartt, LL Bean, Land’s End, etc. make Henleys. They are reasonably priced, come in an array of colors, and are a great basic botton layer. If you like the style, but need short-sleeved shirts, you’re in luck, because they come in short sleeve also.

Rugby Shirts

Rugby shirts are can be traced back to the Rugby school in England in the 1830’s when a player decided to pick up the ball and run with it during a football (soccer) game. As the sport took off and clubs formed, teams started wearing the same shirts to show their unity. Originally made of wool, heavy cotton soon became the standard.

Rugby shirts are generally colorful, frequently striped, and have a contrasting collar. While the body is a knit fabric, the collar is most often a woven cotton. Again, there are an incredible number of brands to choose from, and even more colors and color combinations.

Perhaps the bright colors are part of the reason that rugby shirts crossed over from being strictly preppy to being adopted by the hip hop culture.

Scotland Thistle Rugby Jersey

Preppy Boy - Scotland Thistle Rugby Jersey
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If you are looking for some name brand rugby shirts, check out Tommy Hilfiger, Ralph Lauren, GANT, Noah, J. Crew, Rowing Blazers, Hackett, Gucci, and Thom Browne. As you can see from this list, traditional brands, as well as fashion and street brands have embraced rugby shirts. You can find everyone from Prince Harry to Snoop Dogg wearing them.

A great movie reference for rugby shirts is Michael in The Blind Side. It even shows how preppy crosses into street culture.

Oxford Button-down Shirts

Button-down shirts are another clothing item with its origins in England. Men playing polo found that their collars would flap-up during play. To avoid the interfering and annoying they started using buttons to hold the collars down. John E. Brooks, one of the founders of Brooks Brothers brought the style back to the United States.

Brooks Brothers Original Polo Oxford Cloth Button Down

Preppy Style Men - Brooks Brothers Oxford Polo
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In 1900, Brooks Brothers paired the button down style with Oxford Cloth (a Scottish fabric named after Oxford University). The basketweave fabric became a standard for dress shirts. Originally made in white, oxford shirts have branched out to include blue, ecru, yellow, and pink (or all of the above at once). They present a clean look.

60 years later, President Kennedy popularized pairing the button down with his suits and ties. This brought the Ivy League look to the masses and further cemented the look as an American classic.

But of course, button-downs aren’t just for Oxford cloth. Preppy style is all about the clean lines and functionality so you’ll find plaid and striped shirts that have button down collars. These make great additions to your wardrobe because of their versatility. You add interest if worn alone, or you can pair it with a number of different sweaters or vests. Whether you are using warm colors for fall or winter or brights for summer, a plaid button down shirt is a great addition to your wardrobe without any crooked or flapping collar points.

For a complete button-down collar breakdown visit our guide.

Preppy Sweaters

There are a few basic sweater layers you can choose from to get a preppy look. All come in vest and long sleeve sweater options, and they all can be found at different price points from a multitude of brands. While each is a preppy basic with roots in British style, they have each evolved and can be seen outside Ivy League and prep schools and have seeped into every style imaginable – from the couture runway to street style.

Cable Knit Sweaters

The classic cable knit sweater is a great wardrobe essential. It can be dressed up – paired with a button-down shirt under a sportcoat, or dressed-down – over jeans with a t-shirt or polo underneath.

Luca Faloni Chunky Knit Cashmere Cardigan

Luca Faloni Chunky Knit Cashmere Cardigan

Chunky knit sweaters are a fantastic wardrobe essential when it starts to get chilly outside, suitable for dressing up when paired with a button-down shirt or for dressing down when paired with a T-shirt underneath. But it doesn’t only add interest to your wardrobe; chunky knits, especially made of premium cashmere like the cardigan by Luca Faloni, are the epitome of preppy style. 

Double-fronted pockets, classic horn buttons, and the shawl collar all add to its distinguished and neatly timeless look. Made from 100% prestigious four-ply cashmere, this piece is designed for comfortable layering, your go-to piece come autumn til spring.

Polo Ralph Lauren Cable Knit Sweater

Preppy Sweatshirts Polo Ralph Lauren Cable Knit Sweater
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Whether you choose cotton, wool, or especially cashmere, a cable knit sweater is a great addition to your wardrobe. The cable pattern adds interest, but isn’t necessary for your sweaters. Just a plain wool in either crew or v-neck is a great addition to any wardrobe. Again, you can find these from just about any brand and in any material.

Naadam Essential Cashmere Sweater

Naadam Essential Cashmere Sweater

If you are looking for high-quality, affordable cashmere to add a bit of warmth and luxury to your wardrobe there are some really good brands that are even sustainable (an issue with cashmere).

You can find cashmere at every price point from Naadam’s $75 sweater to those that cost up to $1,000. Be careful purchasing lower priced sweaters because they may be coarse, inferior quality cashmere made in sweatshops. Luckily there are several brands in addition to Naadam that don’t exploit the environment, the goat herders or garment workers yet don’t charge exorbidant amounts for their goods. A bit a research will find you a quality garment you can afford.

A good cashmere sweater will not only last for years, but will add a bit of luxury and a lot of warmth to your wardrobe.

Aran (Fishermen) Sweaters

If you are looking for a bit more rugged, rather than sleek and elegant, you will want to choose an Aran sweater (otherwise known as fishermen sweaters). This is another import from the British Isles; the Aran Islands are off the west coast of Ireland.

These sweaters use a combination of knit stitches such as cable, moss, zig-zag, diamond, etc. to create patterns in wool. Originally, fine merino wool in its more natural state was used. It was undyed and retained its natural oils and lanolin making the sweaters water-resistant. The patterns were individualized so a family’s history as fishermen or farmers could be read in the wool.

For more on Aran sweaters, stitch meanings, and where to find authentic Irish Aran sweaters see this guide.

Aran Woollen Mills

Irish Knit Sweater - Aran Woollen Mills
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Aran sweaters are so iconic that the Museum of Modern Art chose a 1940’s sweater to be one of the 112 pieces in their “Is Fashion Modern” exhibit.

Not only have Aran sweaters been a favorite of classic movie stars such as Steve McQueen, Grace Kelly, and Elvis Presley, but today’s stars like Robert Pattinson, Channing Tatum, and Chris Hemsworth can also been seen wearing them. In fact, Chris Evans spent most of his time in the movie Knives Out in an Aran Sweater.

Aran Crafts Shawl Collar Cardigan

Ivy League Style - Aran Crafts Shawl Collar Cardigan
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While the natural cream color is the traditional Aran sweater look, you can find version of it in other colors, especially neutrals, blues, greens, and charcoal that reflect the Irish Island. You’ll also find these sweaters in vest and cardigan form.

Fair Isle Sweater

Another sweater with it’s origins in the British Isles – this time off the coast of Scotland – is the Fair Isle Sweater. What makes Fair Isle distinctive is the use of double strands of yarn knit to create patterns within the sweater. Fair Isle was popularized by HRH Edward, Prince of Wales in the 1920.

L.L. Bean Fair Isle Sweater

Classic Clothing - L.L. Bean Fair Isle Sweater

Some of the 57 inhabitants of Fair Isle still make sweaters, but today, most are made by other preppy brands or designers like L.L. Bean, Brooks Brothers, J Crew, or Land’s End. Fair Isle has also been embraced by couture designers like Chanel and Karl Lagerfeld.

Fair Isle, while always a classic, transcends that to become more of a trend or fad periodically. In fact, 2023 is one of those times. Fashion magazines from Esquire to Vogue, Spy and GQ have all been writing about the Fair Isle sweater and sweater vest relevance this year.

This is another preppy fashion that has been embraced by streetwear designers. Companies that are transforming fair isle are Loewe, Bowden, and Junya Watanabe.

Junya Watanabe Knit Liner Jacket

Junya Watanabe Knit Liner Jacket

For a resource to genuine Fair Isle sweaters, British makers in the traditional style, and an in depth discussion of everything Fair Isle see this guide. If a fair isle sweater is too much pattern for you, consider choosing fair isle socks or a beanie.

Argyle Sweaters

We’ve gone from knit creating the pattern to patterned color. The happy median for many preppy dressers may be argyle. This is another post-World War I British import made popular by the Duke of Windsor. The overlapping diamond shapes is derived from the tartan of Clan Campbell of Agryll in Western Scotland in the 17th century.

Pringle of Scotland Argyle Merino Jumper

Preppy Fashion - Pringle of Scotland Argyle Merino Jumper

If you want the original argyle, shop at Pringle of Scotland.

GANT Bold Argyle Crew Neck

Preppy Top - GANT Bold Argyle Crew Neck 

Although the style is so popular that you can find some version at most brands like Brooks Brothers, J Crew, Ralph Lauren, and GANT. You’ll often see argyle sweater vests. This is a great, classic look, even under a sport coat. It adds a pop of color and pattern without being too bold.

Argyle can transform from strictly preppy and traditional to street smart and bold.

If you want to add a hint of color, fun, and style to your most traditional business looks, opt for argyle socks.

Sportcoats and Outerwear

You’ve got your shirt, sweater, or vest on. Now you need something to keep you warm and finish the top half of your outfit. You want style and warmth. With preppy style you have a few options that are classics. All can be found at numerous sources in the full price range from reasonable to extravagant. Again, there are classics based on British style and you can find vintage items for authenticity.

The Navy Blazer

A blazer is a sportcoat made of lightweight flannel and may be a bit looser fitting than a sport coat. (Some people mere make the distinction based on buttons. Blazers have metallic and sportcoats have horn.) The navy blazer has its origins in British history.

Queen Victoria visited the HMS Blazer in 1837 and reviewed the crew wearing their short double-breasted jackets in blue with shining brass Royal Navy buttons. This, of course evolved into civilian wear with longer, single- or double-breasted flannel jackets. Today, they also come with either the iconic brass buttons or horn buttons. Both are acceptable.

This is a great look that can be dressed up or down. Whether wearing it with gray flannel pants, a shirt and tie, or a tee-shirt, jeans, and loafer, the navy blazer will complete any outfit. In fact, there is very little that won’t work with one.

Don’t worry about price either – there is a blazer in every price category. If you don’t want to search thrift shops, Amazon has everything from school uniforms to high-end Canali, Paul Fredrick, Ralph Lauren, and Brooks Brothers choices.

Read more about the 16 Best Blazers for Men

Brooks Brothers Milano Fit 2-button 1818 Blazer

Country Club Attire Men Brooks Brothers Milano Blazer
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This Brooks Brothers piece offers the complete preppy look, combining the navy blazer, sweater, button down shirt, and corduroys. Add in a fine watch, the pocket square, and penny loafers and you’re ready to go.

If you are looking for the movie reference, watch Scent of a Woman where the students have navy blazers with a crest on the chest. Further in the movie, the main character, Charlie, is wearing a navy blazer, button down, and tie while at a fine dining establishment.

Tweed and Plaid Sportcoats

Nothing says British establishment more than tweed and plaid. You have Scottish tartans, Harris tweed, herringbone and houndstooth.

Tweeds are the original golf cloths of the early 1900’s. Add some elbow patches and long pants and you have the quintessential Ivy League professor. There are many classic movies that portray this look, notably Goodbye Mr. Chips with Peter O’Toole, a precursor to Dead Poet’s Society.

While you may not know the name of the tweed or plaid you are wearing, you know that paired with a button-down, sweater vest, flannel or corduroy pants and penny loafers gives you the perfect preppy look. Of course, pairing the sportcoat with jeans and a Henley gives you a modern look also. 

Jos A. Bank Tattersall Sportcoat

Country Club Outfits - Jos A. Bank Tattersall Sportcoat

If you are serious about your heritage, and want a tartan plaid that reflects your family’s history, there is a company in Scotland that will design the your fabric. For the ultimate bespoke experience, visit Prickly Thistle.

If you are unsure how to style plaid, visit the Coolist style guide.

Camelhair Coats

If navy or tweeds aren’t your preference, think about a camelhair sportcoat or overcoat. In British terms with would be a polo coat; so named because it was originally favored by polo players between chukkers (in US terms, innings or periods). By the 1920’s camelhair coats were popular with Ivy League students in Princeton and Yale before spreading across the country.

While the original polo coats were more a robe-like wrap, buttons (either single or double breasted) were added, with or without the belt.

Jean-Paul Germain Camelhair Sport Coat

Country Club Prep - Jean-Paul Germain Camelhair Sport Coat
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Camelhair is a wonderfully warm wool, whether you choose sweaters/sweater vests (very preppy), or as an outer layer. It is warmer and more durable than wool and such a classic that they are worth the investment. Though, you can get quality pieces like this one from Jean-Paul Germain at surprisingly affordable prices.

Camelhair polo coats are often found at vintage stores. In fact, they are often favored by fashionistas. Of course, you can find new coats from Ralph Lauren, Brooks Brothers, and many others.

Preppy Pants

So far, we’ve spent a lot of time talking about all the options to cover your upper body. There aren’t as many options when talking about bottoms, but they are all pretty versatile, come in the entire range of price points, and are easy to find at your preferred brand.

Preppy pants are slim fitting rather than baggy, and especially not drop crotch (hip hop style). Look for smooth and elegant. Traditionally your bottoms would be flat fronted, but don’t worry, pleats are perfectly acceptable.


Chinos are actually an American pant based on the military bottoms that armed forces stationed in the Philippines during the Spanish-American War wore in 1898. They were made of a thick twill fabric and dyed a khaki color in China. If you want the real thing, visit Bill’s Khaki’s. The company was founded to bring back traditional cavalry twills that were no longer being made. You can purchase a pair that is based on the same patterns, using the same heavy twills.

ISTO Light Khaki Chinos

ISTO Light Khaki Chinos

When it comes to effortlessly preppy pants, ban those red trousers for life. Earth-toned chinos are the “it” pants, sophisticated, casual, and with excellent repeat wear potential. ISTO has a way of making pants that looks better, comfier, and ultimately longer lasting than the average khaki pants. 

You won’t go wrong with the relaxed but tapered fit, definitely more comfortable, smarter, and style-appropriate than your jeans. Style your chinos with an Oxford shirt or a cable knit sweater for a classic preppy vibe or a simple T-shirt and hoody for an extra cool spin on the style. And when the weather gets a bit hotter, loosely roll up the hems to give you a more relaxed cropped appeal. 

Bill’s Khakis Straight Fit

Vintage Preppy Guys Clothing - Bill’s Khakis Straight Fit

If you are just looking for a comfortable pair of khaki’s you can find them from almost any brand and in just about any color. Really, chinos are just heavy twill pants that are close, rather than baggy, fitting. Docker’s had their heyday making chino’s/khakis a standard part of business casual in the late 1980’s. Paired with a button down (solid or plaid) or a sweater, it is an easy preppy look.


While the origin of corduroy is in ancient Egypt, the modern fabric originated in 19th century Manchester. It’s hard wearing and warm. Thus, it is a common material choice for suits, sportcoats, and pants.

L.L. Bean, Jos. A. Bank, Lands End, and Brooks Brothers are all good sources of everything corduroy.

Corduroy Izod Men’s Corduroy Pants

Essential Preppy Clothes - Corduroy Izod Mens Corduroy Pants
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Corduroy pants are outstandingly versatile, able to pair as well with a preppy sweater or sportcoat as with a casual t-shirt. The exception would be during hot weather, in which case you’d do better with something like seersucker shorts in similar outfits. 

Beware: there are some extremes in preppy clothing that should be used more in moderation. For instance, pants with bold embroideries of boats, anchors, or marine life on them. This is the ultimate in “Preppy” with a capitol P, but really isn’t for most people. It’s also more commonly found on children’s clothing these days where it is perfectly acceptable.

Other Pant Choices

Of course jeans are an acceptable preppy choice, especially if you keep to straight fits that aren’t completely distressed. Raw and selvage jeans are a good choice.

You can also choose any of the fabrics used for sportscoats: gray or navy flannel, tweed and plaids. Stay away from overly baggy and slouchy plants and you have the foundation of a preppy look.

Preppy Shoes

We’ve already discussed preppy argyle and fair isle socks. But what are you going to put them in? There are definitely some shoes that are more preppy than others. Much like the clothing, may have their origins in sporting events.

Penny Loafers & Brogues/Oxford Shoes

If you are looking for preppy dress shoes, they will either be brogues/oxford shoes, or penny loafers. Both are stylish and can be adapted to suits or jeans. If you’re thinking of pair shorts with dress shoes, go with either penny loafers or deck shoes.

Florsheim Midtown Wingtip Oxford

Preppy Shoes - Florsheim Midtown Wingtip Oxford
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Brogues are made from a number of sturdy pieces of leather that tie up. They have perforations and serrations along the piece edges, have heel caps and lace panels – in other words a few more pieces. They are also sometimes called wingtips. Oxford shoes have the same basic construction, although the toe piece is straight across. They often don’t have the perforated patterns. This is a cleaner look.

Most dress shoe manufacturers make brogues and/or oxford shoes. You can even order them bespoke from a number of companies and cobblers.

Honestly, different guides have different definitions of wingtip, brogue, and oxford shoes. However, you can follow our complete guide to Oxford Shoes. What everyone does agree on is that shoes made with more than one color leather are called spectator shoes.

But, if you are looking for something a bit more youthful or less structured you will be interested in penny loafers.

G.H. Bass & Co. Classic Weejun Loafer

G.H. Bass & Co. Classic Weejun Loafer

There are also differing ideas about the origins of penny loafers. The basic construction of an upper vamp stitched onto the lower part of a low (or no) healed shoe is taken from Native American moccasins.

However, some people attribute the design to Norwegian fishermen. That is where Bass Shoes came up with the name of their classic loafers “Weejun”, short for Norwegian. Their theory is that students traveling to Scandinavia in the early 1900’s brought the style back to North America.

The name penny loafer emerged in the 1950’s. Prep school students would wear their weejuns with chinos and sportscoats/blazers and put a couple pennies in the diamond shaped cut in the shoe. It was either a sign of good luck, or having the cost of a phone call on hand.

Boat Shoes

Seeped in the yachting culture, it only makes sense that preppy footwear includes boat shoes.

Sperry Bahama II Boat Shoes

Preppy Men Shoes - Sperry Bahama II Boat Shoes
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Sperry is one of the iconic manufacturers of preppy shoes. Founded in 1935, they have been making their Top Siders for generations of boaters. Today, the shoes have better structure for street wear, but still retain the original aesthetic. If you are a fan of Sperry shoes but want something a bit more stylish, they have joined with John Legend for the Sperry X John Legend collection.

Other common boat shoe manufacturers include: Dockers, Ralph Lauren, Alden, L.L. Bean, Land’s End, and Columbia. If you need even more inspiration, check out our guide to boat shoes.

Duck Boots

Most of the manufacturers that make boat shoes also make Duck Boots. 

L.L. Bean Duck/Bean Boots

Country Club Look - L.L. Bean Duck Bean Boots

They were first created by Leon Leonwood Bean, the founder of L.L. Bean. They were created to keep your feet dry while hunting. Originally made in dark brown with natural colored leather, today they are available in an array of colors with ankle height or lower calf leather uppers. The bottom is rubber and meant to give you traction, be pulled out of the mud and hosed off.

Sperry Saltwater Duck Rain Boot

Southern Prep Fashion - Sperry Saltwater Duck Rain Boot
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But of course, other classic preppy brands have their own version of the duck boot. We like the fabric-topped Sperry Saltwater Duck as a waterproof value alternative, but Skechers, London Fog, Land’s End, and many other manufacturers have options worth considering.

Further Reading: The Best Waterproof Boots of 2023

Wellington Boots

If you’re working in the stable you still need waterproof boots. You just need them without the leather and much higher. Like most things preppy, Wellies have their origins in British culture.

They are named after the Duke of Wellington who wanted a modified version of the traditional Hessian boot that was used for riding, but were more comfortable and durable. Luckily, Hiram Hutchinson and Charles Goodyear invented a way to vulcanize rubber in 1852 making it waterproof. When the Duke’s design was combined with the new material, the Wellington boot was created.

Originally marketed to rural farm populations, they became the footwear of choice for trench warfare soldiers in World War I. And, after World War II, Wellies were adopted by gardeners and fishermen.

Hunter Original Short Rain Boots

Hunter Original Short Rain Boots
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Today, Wellies are made in a variety of colors by a variety of manufacturers. You can still purchase the original North British Rubber Company boots (Uniroyal Limited since 1966), but Hunter Original Rain Boots are a preppy-yet-functional pick.

Like Duck boots, you can find them in various colors from various manufacturers, or choose the original. Regardless, they are a part of preppy history.

Preppy Goes to the Movies

If you are more of a visual learner, there are tons of movies that will give you a picture of preppy and the preppy lifestyle.

The most obvious movies are those that center around prep schools. Dead Poet’s Society, School Ties, and Scent of a Woman are good examples of boy’s schools. For women, you can watch Mona Lisa Smile. Many of the 1980’s movies also show preppy style: Ordinary People, Jake in 16 Candles, Brian in The Breakfast Club, and even some of the characters in Caddyshack. It’s pretty obvious that preppy is everywhere.

Preppy Brands We Recommend

Some Traditional Manufacturers to explore:

  • Alden
  • Brooks Brothers
  • Drake’s
  • Hackett
  • J. Press

Some Modern Takes on Preppy:

  • Beams+
  • GANT
  • J Crew
  • Noah
  • Ralph Lauren
  • Rowing Blazers
  • Tommy Hilfiger

Preppy Style Guide: Final Thoughts

Preppy means many different things to different people. To some, it is an ugly throw back to snobbish society. To others it is the quintessential guide to successful dressing.

Either way, the separate pieces that make up preppy clothing are all functional building blocks to a versatile wardrobe. Whether you choose to embrace one or all of the pieces in this guide, each is as fashionable and comfortable as it was when first introduced.

Not only does the style reflect the prep school and Ivy League aesthetic of yesteryear, it has been refined, updated, and adapted to encompass everyone from every walk of life – from professional academic to street smart musicians.

So, what do you consider a preppy fashion essential? Do you have any specific suggestions for preppy mens clothes we didn’t mention or feature? What are your favorite preppy brands? Leave us a comment below!