This guide is about prep clothing & preppy style. It’s not exclusive to those who attend or are alumnus of Ivy League schools and preparatory academies in the Northeast United States — it’s for everybody interested in this (life)style.

Prep Style Video

What Does Prep Mean Traditionally? Old Ivy League Money!

Traditionally the terms “prep,” “preppy,” “prepster” or any other variation was historically used to describe a subculture of upper class youth born into old money in the Northeastern United States. They, as their fathers before them, would attend the family alma mater, typically one of the eight schools classified as “Ivy League:” Brown University, Columbia University, Cornell University, Dartmouth College, Harvard University, Princeton University, the University of Pennsylvania, and Yale University.

Can You Be Preppy Without Having Been To Ivy League Schools Today? Yes!

Today, the term “preppy” is far looser and is a term regularly used in high schools across North America and parts of Europe. It still describes a subculture, but that of a social circle of well brought up men and women who have adopted a manner of speech, vocabulary, dress, manners and etiquette that becomes an integral part of their lifestyle, which is reflective of the traditions adopted from those historic upper-class Northeastern families.

Of course, the prep culture or coastal culture is still very predominant in those regions, but it has spread into other areas and is often referred to as southern culture and now classic American culture, adopted by men and women in all of the fifty states, as well as abroad.

The Official Preppy Handbook Started Out As a Parody

One way to explain the culture is to compare it to dandyism. If you haven’t read Lisa Birnbach’s books The Official Preppy Handbook or True Prep, buy them today as they’re the primers you’ll need on what it means to be a prep. What is interesting, however, is that when Birnbach wrote the book, she intended it as a way to poke fun at the privileged East Coast college students she grew up with, but it ironically ended up glamorizing the prep culture —which was really the beginning of spreading it throughout the United States and into other countries.

Prep Style Explained

One relatively tell tale sign of a prep is the sense of the style adopted by the average preppy. Almost like a school uniform, the culture has adopted a very nautical, clean cut image synonymous with brands like Brooks Brothers, J.Crew, LL Bean, Ralph Lauren and other various brands. Just as Christians go to Church, executives go to the boardroom and astronauts enjoy going to space; we as preps will forever enjoy the breeze on the boardwalk, the gin and tonic in the backyard and soaking up the sun in the summer.

At Gentleman’s Gazette, many readers define themselves as well-dressed whereas other readers will agree they fit into the subculture of being a true prep.

An Introduction to Prep Style

Before you go assuming that we’re different from other subcultures, stop and think. As bikers wear leather and tattoos, rockers wear tight leather and band shirts, and cheerleaders wear pink, we as preps enjoy a certain style all our own. It defines us and gives us the ability to showcase the things we’re passionate about, in unobtrusive ways but while being able to say “Hey, I’m a prep and I’m proud of it!”

Taking inspiration from the Ivy League styles of the past and the nautical flair of many East Coast villages, prep style has evolved but stayed much the same since the mid eighties. We’re more than just bow ties, boat shoes and madras. We’re about passionately showcasing the styles of some of America’s most established and iconic haberdasheries.

History of Preppy Style

The initial preppy style actually started around 1910-1912 before becoming popularly known as Ivy Style in the mid-1940s. One of the first and most iconic preppy brands, J. Press, began to develop fashions that were sold exclusively to the various Northeastern collegiate and many believe that it was that J.Press that helped to shape the preppy subculture we know today. By the mid-twentieth century, the two most iconic preppy haberdasheries had developed storefronts on campus at Harvard, Princeton, and Yale. It was Brooks Brothers and J.Press that started the trends, giving affluent Ivy League students onsite shopping, which resulted in much of the campus wearing their clothing.

With the popularity of traditional New England activities such as sailing, fencing, rowing, tennis, golf, and polo, many of the fashions that were designed for sale on campus were reflective of these leisurely pastimes. Since much of the clothing sold were influenced by these activities, it stood to reason that students on campus began wearing the clothing to those respective events, matches and games. Since students often spent much of their off-campus time together, many of them traveled with their families to Palm Beach, Florida, which really became the quintessential preppy vacation hotspot. It was here that many of the companies outfitting these Ivy Leaguers were inspired to begin using the bright colors found in Palm Beach in their clothing, a contributing factor to why preps are so well known today for wearing such brightly colored attire. By the 1980s, preppy style was in a class of its own with dozens of companies opening up shop to cater to a wealthy clientele who treated clothes with a passion hardly seen in America before.

Top designers in the mid 1980s began to catch on to this trend and started designing professional wear for women in New York who as students developed a love for the prep subculture. Classic attire such as tailored skirts, suits and dresses began to adopt nautical and equestrian elements with pops of pastel colors. Hollywood was in a boom and some of its leading ladies were the most well known preps of the time including Grace Kelly, Audrey Hepburn and Jacqueline Kennedy. It’s due to their vested interest and subsequent advertising of the prep culture that many credit with the bold and colorful clothing well known for being worn throughout much of the 1980s.

Today, there are entire companies dedicated solely to creating prep fashions for men and women. Read further for the list of my favorite designers.

Prep Clothing – What To Wear

There are many items we enjoy as a whole. Often some of the best items are handed down, and many are found in little antique shops and thrift stores.

In the following list, Sven Raphael Schneider & J.A. Shapira discuss some of the most popular preppy wardrobe items:

Anchor Bracelets

Anchor bracelets are exactly what they sound like. Bracelets made of a variety of fabric and materials, usually rope, leathers or sail cloth and fastened with a small metal or plastic anchor that operates similarly to a hook. This jewelry is very popular in prep culture both with men and women and is about as nautical as it gets.

Argyle Sweaters

The argyle sweater is predominantly seen in golf apparel, which is why it has become so ingrained in the prep culture. Since golf has long been a favorite pastime of preppies, Argyle has become a pattern fashionable amongst both men and women. The pattern itself can simply be characterized as being made up of diamonds or lozenges. Typically they will overlap in a motif which can add a sense of multiple dimensions and texture. In most cases, it’s used as an overlay of intercrossing diagonal lines on solid diamonds.

While you can find these patterns in solid blacks and grays, what’s most popular are the bright colors including blues, greens, and pinks.

Barbour Wax Jacket

Barbour wax jackets are extremely popular with Prep’s, and they have been for years. Most people choose between the Beaufort, which was designed for shooting (hunting for all Americans) with an extra game pocket and the Bedale, which was made for horseback riding. To go over all pros and cons of each model, will be worth an article on its own, especially considering the option of different waxes, cuts, aging and submodels. However, we think the classic Beaufort in olive green will work for most men.

Belts

Colorful belts with motifs and stripes are an integral part of a preppy wardrobe. Often combined with brown leather and a brass buckle, these more or less flexible cloth belts are combined with chinos, Madras or seersucker pants to create a bold look.

D-ring or Ribbon Belts

D ring belts have been around since the mid 1960s when introduced by J.Press. They provide a casual and fun flair to a normally conservative look. Some say that in order 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.

Traditionally called a “Ribbon Belt,” the newly-coined term “D-ring” is believed to have been made up by Vineyard Vines, one of my favorite companies catering to the preppy lifestyle. In the sixties, during the height of hippies, privileged and traditionally conservative East Coast preps used the colored ribbon belts as a way to add some more personality to their dress. There’s nothing exclusive or luxurious about ribbon belts. They’re just a lot of fun with various patterns. From the iconic tri-stripe belts and the five-stripe versions from Ralph Lauren to ones with embroidered lobsters and sail boats lining them, the belts, although traditionally made of polyester, rayon and nylon, now come in a variety of fabric and materials from sailing cloth to fine cordovan leathers.

Boat Shoes

Like many staples in prep style, you either love boat shoes or hate them. Personally, I adore them. In fact, as I sit in my office writing this article, I am wearing a pair of boat shoes by Brooks Brothers. While many credit Sperry Topsider with the initial introduction, and most people consider them the quintessential boat shoe, there are many companies today that make them. Boat shoes are pretty much exactly what they sound like. They were created as a non-slip shoe for sailing and are generally are made of leather and sometimes suede or other materials. They are worn exclusively without socks and as a casual shoe that is tied using leather boat shoe laces. For more information, check out this great primer on boat shoes by my colleague Sven Raphael Schneider.

Cable Knit Sweaters

Cable knit sweaters are classic and will never go out of style. No matter whether they are made of cotton, wool or cashmere, with sleeves or without, they are a staple of a preppy wardrobe. If you wear bow ties, a crew neck is the way to go, 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. Of course, just like with any other sweater quality is paramount but we will write an article just about that, so stay tuned.

Tennis & Cricket Sweaters

Tennis or Cricket sweaters are a must-have in a preppy wardrobe. Take a look at our dedicated Tennis sweater article here.

Chinos

Chinos are trousers made from chino which is a twill fabric, originally made of 100% cotton. While they can be found in synthetic blends now, the best are still made of cotton. Brooks Brothers offers a superior selection of them as do many other fine clothiers. Today, they come in many colors, but the most common is khaki which is still very popular in coastal culture.

Madras

Madras is also a cotton fabric that is generally very lightweight and features a textured plaid design. For details, see our Madras Guide. Aside from pants, you can also find many shorts and even mens jackets made of it. The Madras pattern is available in regular cotton, seersucker as well as patchwork madras which consists of cutting the madras fabric into strips and then sewing them back together to form a mixture of patterns that criss cross. This is very popular in the prep culture and something widely used by Brooks Brothers, among other fine mens haberdashers that focus on prep style.

GTH (Go To Hell) Pants

Some love them, others hate them, and there is little in between.

GTH pants take some serious getting used to. This is a style of its own and one that will surely net you looks of disdain and nods of approval as you walk around in them. These are bright pants with sometimes bold embroideries on them of sailboats, anchors, lobsters, crabs, frogs and a variety of other icons. They are obnoxious but so much fun to wear! Brooks Brothers once said that it’s like playing a game of chicken with your friends except no one goes off a cliff. Instead, the winner is viewed as the most daring dresser around. Just use some caution with what you pair with them.

For more details, please check out our go to hell pants guide.

Loafers

Loafers, like boat shoes, are synonymous with coastal culture. There are a variety of loafers on the market from the most casual forms to semi dress shoes. They are typically categorized as being a low, lace-less shoe that you slip on and wear out, rather than as a slipper indoors. Traditionally, loafers are a casual shoe, but recently many preps have begun wearing them with lounge suits or to work at offices with a more relaxed dress code. They come in a variety of styles, colors and materials and occasionally will feature tassels or decorations on the front of the shoe. For a detailed discussion of loafers in all their varieties, read the Ultimate Loafer Guide.

L.L. Bean Boots

Founded in 1912 by Leon Leonwood Bean, and quickly known for their boots. Originally, they were hunting boots made of rubber and organically treated full grain cowhide to resist water. The characteristic look was achieved by a crepe rubber sole and contrasting brown or tan uppers. While most boots today are lined with Gore-Tex, back then a simple wool lining was the norm. Many would give an arm and a leg to find new old stock boots in their size, but even the current version of their boots is so popular that the annual sales of the company are north of 1.5 billion. Of course, they now sell all kinds of other outdoor-related items, but the Bean boots in different heights and variations are still a favorite with preps.

Nantucket Reds

Corn dogs are to carnivals what Nantucket Reds are to prep culture. The red pants, shorts, shirts, hats, and various other articles were originally distributed by Murray’s Toggery Shop in Nantucket and are “guaranteed to fade” to an almost rosy pink. They are traditionally pants, but today consist of an entire selection of clothing and accessories that are incredibly popular to the point of being legendary in Martha’s Vineyard, Cape Cod and their birthplace of Nantucket.

Classic Navy Blazer

This is perhaps the most iconic piece of menswear worn and designed to be worn by preps. Although available in a variety of styles, the standard is a navy single breasted jacket with notched lapels and three brass buttons, often with an icon or logo that is nautical in nature or represents the brand. Of course, many companies make these blazers but the most popular today seem to be from Ralph Lauren and Brooks Brothers. Since it is such a classic you must read the Blazer Guide.

Oxford Button Down Shirts

Button-down collars were initially introduced by Brooks Brothers in 1896 and have remained popular as a way of dressing down the dress shirt. Using buttons that fasten down the collar points on the front of the shirt, they were almost exclusively worn as sport shirts until the mid 1950s. Still considered a sports shirt in most circles, or as a way to give casual flair to elegant attire, these shirts are extremely popular in prep culture and are often paired with the iconic navy blazer and a repp tie.

Polo Shirts

Polo shirts, which are often referred to as a golf or tennis shirt, are a well-known staple in prep style. A casual and soft shirt with a collar, a placket, and usually two or three buttons, it can often feature a breast pocket as well. Made from knitted piqué cotton, it can also be found in silk, merino wool, or various synthetic materials. These shirts are often worn with a pair of shorts or trousers but can also be paired with a blazer or sports jacket. Make sure not to miss the Ultimate Polo Shirt Guide with 6 videos.

Quilted Jackets

Just like wax jackets, quilted jackets are a popular staple in a prep’s outerwear collection. To learn more about them, read out Quilted Jacket Guide.

Rugby Shirts

Although Rugby is quintessentially British, many preps like to wear rugby shirts probably because the aesthetic of bold colorful stripes and a white collar is very much in line with other preppy clothing items.

Seersucker

Seersucker is another iconic fabric used in prep style. For details check out our seersucker guide. As a thin, cotton fabric that’s usually striped or checkered, it’s predominantly used to make summer clothing such as suits, shorts, pants and other men’s and women’s clothing. Originating from India, the word seersucker literally translates to “rice pudding and sugar” which is pretty well what it resembles. Because of the way it’s woven, the threads often bunch together which gives it a wrinkled appearance. It’s because of this bunching that the fabric sits away from the skin when it’s worn which helps to keep the body cool, since it enhances circulation and dissipation of the heat. In other words, it’s bloody fantastic to wear in the hot summer months – especially if you need to wear suits at work.

Sport specific leisurewear such as golf, tennis, cricket, rugby, sailing and equestrian apparel.

This particular area is quite vast, from cricket sweaters and vests to rugby shirts and shorts, virtually any item of clothing you see being worn at a predominantly preppy sport can be considered an integral part of prep culture and fashion.

Ties & Bowties

Not exclusive to prep style, we’ve managed to adopt our own style however with various old boys club style repp ties and bow ties of the same design or wackier icons including sea critters or sports icons. We wear them loud, and we wear them proud.

Tweed

During fall winter, a true prep can rarely be seen without any form of tweed. Instead of giving you all kinds of tweed advice here, head over to our ultimate tweed guide and enjoy.

Vests

Contrasting vests in madras or moleskin in more or less intense colors are an excellent way to polish your preppy outfit. You can find all you need to know about vests & waistcoats in our vest guide.

White Shoes

White buckskin shoes aka white bucks are a popular preppy companion to seersucker pants or cocktail parties, horse races or anything else related to summer. Paired with linen, chinos or seersucker they provide the wearer with a debonair, seasonally appropriate look. Buckskin leather is technically from the male deer but today often cowhide is used instead because it is less expensive and more widely available. In the U.S. most buckskin shoes show the backside of the leather, which has a texture similar to suede, but we think the front side of buckskin leather is very nice as well. Many white bucks come with a lightweight, red rubber sole although we prefer the classic leather sole goodyear construction.

Make sure to check out our Men’s Summer Shoe Guide for more details.

Preppy Style Brands

* Denotes a personal favorite and recommended brand of J.A. Shapira

Anchored Style

Atlantic Drift

Bird Dog Bay*

Boast

Bourbon & Bow ties

Brackish Bow Ties

Brooks Brothers*

Castaway Clothing*

Chubbies Shorts*

Coast

Collared Greens*

Criquet

Daniel Wellington (classic preppy watches)

Dapper Classics (preppy dress socks)

Dogwood Black

Frat Collection

Frank Clegg (leather goods)

Fripp & Folly

Gameday Blazers

Harding-Lane

Hatley

High Cotton

Hudson Sutler

J. Crew*

J. Press*

J. Riley

Jack Donnelly Khakis

Kiel James Patrick*

Knot Clothing Co.*

Krass & Co.*

L.L. Bean*Lazyjack Press

Lemon & Line*

Lilly Pulitzer* (can’t not be mentioned, despite focusing on women’s wear)

Murray’s Toggery Shop (home of the Nantucket Reds)

Old Try*Onward Reserve North River Outfitters Over Under Clothing

Pendleton Woolen Mills

Ralph Lauren

Red’s Outfitters (sunglasses)

Rowdy Gentleman

Saint James

Salmon CoveSebago

Sloane Ranger

Smathers & Branson*

Social Primer*

Southern Frock

Southern Point Co.

Southern Proper*

Southern Shirt Co.

Sperry Top-Sider*

Starboard Clothing Co.*

Vineyard Vines*

More Preppy Resources

Take Ivy, the book about Ivy League Prep Style from the 1960’s.

True Prep and The Official Preppy Handbook

IvyStyle.com – Online blog all about prep culture and Ivy style.

RedClaySoul.com – Online blog all about prep culture.

UnabashedlyPrep.com – One of the best of its kind, a great blog about preppy culture.

FivePointFox.com – A blog all about classic prep culture.

ClassyGirlsWearPearls.com – Despite being geared to women, it remains one of my favorite blogs about prep culture.

Ivy League Style – Pictures of Ivy League Style

The Daily Prep – the name says it all

Conclusion

Preppy style is more than just fashion, it’s a lifestyle and an entire subculture. It’s widely adopted in America and other parts of the world and the information available on it is so vast it has managed to fill entire books. We’re going to continue this series in an effort to talk about the entirety of the culture, including reviewing specific products and companies that have become synonymous with the culture itself. If you are interested in learning more about it, I wholeheartedly recommend the “bible” being the books True Prep and The Official Preppy Handbook, both of which are written by the famous and incredible author Lisa Birnbach. They are very tongue-in-cheek, but offer a great glimpse into the “old new world” as she calls it. Stay tuned for our next article in this series where we’ll talk a little about the cultural side of being a prep.

Did we miss anything – a clothing item, a brand etc. ? Please share your thoughts in the comments below!