Thomas Payne Chronicles

A Guide To A Preppy Gentleman

A Guide To A Preppy Gentleman

A Prelude to Prep
First things first, this guide isn’t intended exclusively for the alumnus or attendees of Ivy League schools in the northeast United States. To be honest, I myself never attended an Ivy League school, I wasn’t brought up on the East Coast and growing up I was early to learn that we were a comfortably suburban and middle class family. To put it in another way, I didn’t have a trust fund growing up, and my 'gold card' is from Starbucks. But to dress preppy isn't where you come from, it's who you are. It's how you want to be.

Usually when we hear the terms “prep” or “preppy” or even “ prepster” along with other variations of such terms which have been used to describe a the subculture belonging to the elite upper class youth whom were fortunate enough to be born into old money. These families, usually situated in the exclusive northeastern United States and as their fathers and forefathers before them would attend the alma matter of the family usually going to one of the eight schools classified as the Ivy League; Brown, Cornell, Columbia, Dartmouth, Princeton, Harvard, Yale and the University of Pennsylvania.

Although today the term has become somewhat looser, it still identifies that subculture but that of well brought up men and women who have accustomed themselves to using a certain manner of speech, vocabulary, etiquette, mannerism and dress, as an integral part of their life reflecting upon the traditions that were adopted from the historic upper class Northeastern families.

The prep culture or the coastal culture as I call it, happens to be very predominant in the region still but it has also spread out to other areas and is now referred to as southern culture and even the classic American culture often as it has been readily adopted by men and women belonging to all of US’s fifty states and even abroad.

One of the best ways to explain the prep culture would be to compare it to what we know as 'dandyism'. If you haven’t had the chance of reading Lisa Birnbach’s books titled Official Preppy Handbook or True Prep, go ahead and buy them right away because they’re what you need to understand how to be a prep. The most interesting thing however is that although Birnbach sought to poke fun at what she referred to as the privileged culture of the East Coast college’s whom she grew up with, she ironically ended up making it appear all the more glamorous and becoming one of the main causes of spreading the prep culture throughout the United States and also to other countries around the world.

I am often characterized as being preppy, which I happen to be really very proud of because I am a very staunch believer of the backbone of this culture. For me it isn’t about wealth that shows in pictures but more about the etiquette, the style, the food, the drinks and also the ethics and morality. It's more than fashion, it's a lifestyle that highlights the very best of what you see in society. 

One of the most visible sign of prep is the sense of style that is adopted by all preppies. This happens to be very similar to a school uniform as the culture is all about a very crisp and clean image. As customary as it is for the Christians to go to church, the astronauts to go into space and executives going to the boardroom, we the preppies all enjoy summer breeze on boardwalk, gin and tonic in their backyards and some good sun soaking moments during summers. Trust me, as prep as I am, I would jump on every chance I get to spend my summer in Cape Cod or Hampton’s.


An Introduction To Preppy Style

Don’t assume the prep culture to be different than the other subcultures. Just like the bikers wear leathers and tattoos, the cheerleaders wear pink and the rock stars wear tight leather and band shirts, the preppies enjoy a certain style of their own. This particular style, gives us, the preppies, an ability to show what we are passionate about without being over the top and in people's face with what we have determined to be the ultimate lifestyle.

Prep style certainly has taken its fair share of inspiration from it's inception in the Ivy League hallways and East Coast villages and although it has evolved since the mid-eighties but it has certainly retained its original flair from the past. We’re prep and we’re certainly more than plain bow ties, madras and the boat shoes. You can say that we’re passionate about showcasing our style that we’ve picked from America’s most established haberdasheries.


History of Prep Style

The first preppy style actually took birth somewhere between 1910-1912 and then became popularly known as the Ivy Style during the 1940s. One of the first preppy bands, iconic ones too, J. Press actually developed fashions during this time and sold them exclusively to northeastern collegiate shaping what we know as the preppy subculture today. During the mid of the twentieth century, a number of iconic preppy haberdasheries had developed their storefronts on campus at Princeton, Yale and also Harvard. The credit for starting the trend actually goes to Brooks Brothers and J. Press and thanks to them the students had an onsite shopping platform where they could buy and flaunt their affluent style while attending college.

Fashions sold in storefronts and by popular haberdasheries during the time focused on reflecting the popular pastime activities of New England such as fencing, sailing, rowing, polo, tennis and also golf. And since the clothing items were influenced by these activities, students began actively wearing them to respective games, events and matches. Most of the students spent their off-campus time together and traveled with families to spots like Florida and Palm Beach which then actively gained the reputation of being the preppy vacation hotspots. This was where these brands found their inspiration for preppy clothing and all preppy clothes then began to feature bright colors. When the 1980s hit, preppy style had become a culture in its own and dozens of companies had open up to cater to a long list of wealthy clientele who focused on clothing more passionately than America had ever experienced before.

Top notch designers focused on this trend too and started creating preppy clothes for the women students as well who in their own selves had developed a love for the prep subculture. Tailored skits, dresses, suits and other classic wear items began to feature equestrian and nautical elements with bursts of pastel colors. Hollywood soon followed the prep trend with a boom and some of the leading ladies of the time including Audrey Hepburn, Grace Kelly and also Jacqueline Kennedy happened to be prep icons. It is because of their vivid interest in subsequent advertising of the preppy culture that a lot of people credit them with the bold and vivaciously colorful clothing that was worn throughout the 1980s.

Today there are entire brands and companies focused on creating prep fashion clothes for men and women. Read on and I’ll give you a list of my favorite designers.


Preppy Clothing- What We Wear

There are a number of items that we love wearing. Often we are handed down the items we love from within the family or you could just be lucky and find that preppy item in a little antique shop or perhaps from a thrift shop.

Here’s a list which feature some of the most popular preppy wardrobe items:

  • Anchor Bracelets

If you’re looking for a strict definition of anchor bracelet, the term is used to describe a bracelet constructed out of nylon sailing rope. Instead of a traditional toggle, ring or claw clasp, these bracelets are secured by ornamental metal clasps shaped like anchors.

Many types of men’s bracelets have symbolic meaning. For example, gemstone bracelets for men may represent certain months of the year or be associated with certain forces or personality characteristics. There really is a symbolic anchor bracelet meaning that is quite the same as the type of meaning that is associated with other types of bracelets. Extremely popular with coastal towns, these bracelets celebrate the rich heritage of the nautical history of the Northwest fishing communities as well as a homage to yachting, rowing, and other nautical sport based in the traditional culture. 


  • Argyle Sweaters

This is a popular golf apparel item and thus specifies why it has been included in the prep culture. Golf happened to a favorite pastime of all preppies and therefore argyle sweaters became a huge fashion amongst men and women belonging to the culture.

The pattern is made and characterized by lozenges or diamonds and overlap in a motif giving a sense of multiple dimensions in one. Usually it is an overlapping of intercrossing lines drawn diagonally on a solid diamond. The best thing about argyle sweaters, the pattern can be found on blacks, grays and even bright colors like blues, greens and also pinks.

  • Barbour Wax Jacket

These jackets happen to be extreme favorites of all preppies. There is the Beaufort (an extremely beautiful jacket designed especially for hunting providing extra game pocket) and Bedale (made especially for horseback riding).

The pros and cons of both need a separate space to be discussed however if you ask me, I’d say a classic Beaufort in olive green would be amazing for most men.

  • Belts

Vivid colored belts with stripes and motifs are a very popular part of the preppy style. These patterns are usually combined with leather and brass buckles. The preppy belts go pretty well with chinos, seersucker and also madras pants when you want a bold look.

  1. D-Ring Or Ribbon Belts

D ring belts have been a part of preppy culture since they were introduced by J. Press in the 1960s. they can be used for a normal conservative or a fun flair casual look as well. Well to be honest, to wear a D ring belt you need a solid sense of humor or perhaps a small budget because these are reversible, giving you options for two belt styles in one.

The D-ring belt or a ribbon belt as it was previously known are made by Vineyard Vines, one of my favorite preppy style companies that have been catering to the prep fashion since the sixties, the time of hippies. East Coast preps used these ribbon belts to add personality and color to their dress styles. One thing that you should know is that there isn’t anything luxurious about the ribbon belts but they’re a lot of fun because of their vivid patterns. There were the tri-stripe belt and the five stripe belt from Ralph Lauren and others that happened to be all-time hits featuring embroidered sail boats and lobsters and made from rayon, polyester and nylon. Today you find a lot of choices amongst ribbon belts from those made from sailing cloth to fine cordovan leathers as well.

  • Boat Shoes

If you’re  a true prep, you’ll either love the boat shoes or hate them. For me, they’re one fine item. In fact while I’m typing this here I am wearing a pair of good old boat shoes by Brooks Brothers. Sperry Topsider happened to be the first to introduce them long ago to the prep culture however there are a number of prominent companies that make the quintessential boat shoes today.


These boat shoes are just like what they sound; made from leather or suede, these were non-slip shoes especially made for sailing. Boat shoes are worn without socks and can be used as a casual shoe that’s tied with laces.

  • Cable Knit Sweaters

These are classics and will never ever go out of vogue. They can be made from cotton, cashmere, wool and can feature sleeves, be sleeveless or whatever but they are a very integral staple of the preppy wardrobe. You can wear bow ties with crew necks while ties will go great with V-neck sweaters. If you’re looking for a casual outfit then perhaps you’ll need a mélange two tone yarn which gives the sweater a very gentle look.  Quality is of utmost concern and we’ll soon feature a complete article for that so until then stay hooked.

  • Tennis and Cricket Sweaters

These are must have items in preppy wardrobe. You can take a look at our Tennis Sweater article for more information.

  • Chinos

Chinos are trousers made from a fabric called chino which happens to be twilled and made from 100% cotton. They can now be found with synthetic blends but the best ones still feature cotton. If you want a superior collection, Brooks Brothers are what you need. You can find chinos in a lot or colors today but the most favored ones are still in khaki.

  • Madras

This is also a very lightweight cotton fabric featuring a textured plaid design. You can see our Madras Guide for more information. Pants aren’t the only item you’d find in madras; shorts and jackets are also made from this fabric. The madras pattern can be found today in seersucker and cotton and there is the patchwork madras which is made from cutting madras fabric into stripes and then sewing them back to make a crisscross pattern. Madras is highly favored by all preppies and available in abundant designs at Brooks Brothers more significantly amongst all other men haberdashers of the prep style.

  • Go To Hell (GTH) Pants

These are a personal favorite whereas my mom and my wife simply hate the look of them. I just don’t get to wear them because I don’t run the household but they are some serious clothing item that you can learn to adore. GTH pants have a style of their own and you can earn either nods of approval or disdain while you go about wearing them. These pants are brightly colored and feature ridiculously silly embroideries on them like anchors, lobsters, sailboats and a lot of other icons. Yes, these are obnoxious but certainly amazing to wear. Its like playing a game of chicken with your friends yet no one gets off a cliff, as per Brooks Brothers. And the best part? The winner of the game happens to be the most daring dresser in the pack. If you’re going for GTH pants just be cautious with what you pair with these babies.

  • Loafers

These go hand in hand with the coastal culture. You can find a whole range of variety of loafers in the market featuring casual to semi formal dress shoes. Loafers are low, lace less shoes that you can simply slip on an go out. Although loafers are casual shoes but recently executive preppies have begun wearing them with lounge suits to work for a relaxed dress code. You can find a whole range of loafers  featuring a wide variety of colors, styles and materials in the market. We have the Ultimate Loafer Guide if you want more information.

  • L. Bean Boots

These were founded by Leon Leonwood Bean in 1912 and were originally hunting boots made from rubber and treated with cowhide to resist water. The characteristic look for these boots was achieved by giving them a crepe rubber with contrasting uppers in brown or tan. Today you can find these boots lined with Gore Tex, whereas a simple wool lining happened to be the norm in old times. True preppies would perhaps agree to give an arm and leg to find the new old stock boots in their size. The current style however is no less popular either and this can be proved by the fact that the company’s annual sales happen to be somewhere near 1.5 billion. You can find all types of outdoor related items with the company but the authentic preppies favor the Bean boots even today.

  • Nantucket Reds

Can you imagine a carnival with corn dogs? No, right? Similarly prep culture is incomplete with Nantucket reds. The red pants, shirts, shorts, hats and other items were originally distributed by the Murray’s Toggery Shop in Nantucket and eventually yet guaranteed faded to a rosy pink. Traditionally Nantucket reds happened to be pants but today you can find a whole range of clothing and accessories that have become as popular as the legendary in Martha’s Vineyard, Cape cod.

  • Classic Navy Blazer

This is an authentic prep wear. Although there are a variety of styles, the standard happens to be a navy single breasted jacket which has notched lapels and three brass buttons along with a nautical or nature logo representing the brand. There are a lot of companies which manufacture navy blazers today but the finest ones will be found with Ralph Lauren or Brooks Brothers only.

  • Oxford Button Down Shirts

These were initially introduced by Brooks Brothers back in 1986 but have remained a very popular prep wear item. These were worn commonly as sports shirts till 1950s because of the buttons that were used to fasten the color points on the shirt front. If you want to give a casual flair to your elegant clothing, this is what you need coupled with a navy blazer and a repp tie.

  • Polo Shirts

These can also be called the tennis or golf shirts and happen to be an important part of the prep wardrobe. Polo shirts are causal shirts with a color, a placket and feature two to three buttons. A number of styles feature breast pockets as well. Usually made from knitted pique cotton, polo shirts can be found in merino wool, silk and a number of other synthetic materials as well. Polo shirts look great when coupled with shorts or trousers alike and also under blazers and sports jackets.

  • Quilted Jackets

Just like there are wax jackets, the quilted jackets are also an important item in the prep culture outwear collection.

  • Rugby Shirts

Rugby happens to be British in descend but preps from around the world favor rugby shirts as an authentic part of the prep style. This is mostly because of the aesthetic bold stripes and white colors that is very much in alignment with the popular preppy style.

  • Seersucker

This is another very popular fabric used in preppy style. Seersucker is a fabric that is thin, made from cotton and has a striped or a checkered pattern and is commonly use to make summer clothes such as shorts, pants, suits and other items both for men and women. Seersucker originate from India and literally mean rice pudding and sugar because this is what it resembles. The threads of seersucker often bunch together giving it a wrinkled appearance because that’s how its woven. The fabric therefore sits away from the skin allowing it to stay cool and also enhances the dissipation of heat. In short seersuckers are what you should wear when the weather is hot and you’re in need to look cool.

  • Sports Specific Leisurewear

This area is enormously vast and features items from cricket sweaters to rugby shorts. To be more precise, any item that you see prominently being worn at a preppy sport happens to be an integral staple of the prep style culture and fashion.

  • Ties and Bowties

These aren’t exclusive to the prey style but the style has been adopted well with old boys club style repp ties and bow ties. The ones that preppies favor have wacky icons including sports, nautical or sea critter logos. Preppies wear bowties/ties loud and proud.

  • Tweeds

No true prep is seen without tweed in winters. Read our ultimate tweed guide to know all there is to know about them.

  • Vests

We favor contrasting vests made from madras or moleskin. We focus on less strong colors because that’s how our outfits are polished.

  • White Shoes

White buckskin shoes, also known as white bucks are a very important prep wear item. They are to seersucker pants what cocktails are to a cocktail party. White shoes can be paired with linen, chinos and seersuckers to give a very seasonally appropriate debonair look. Originally buckskin leather was used in the manufacturing of the white bucks but today cowhide is also used  for white bucks to make them more affordable and readily available for all in the US. The best thing about white bucks is that they are extremely lightweight and comfortable to wear for years.



Preppy style isn’t just a fashion. It’s a complete lifestyle and a comprehensive subculture. This style is popularly adopted in America and other parts of the world. The information about prep culture would be enough to fill in hundreds of books in a row. We will continue this series to let you know about prep culture in its entirety including reviews of specific companies and products that have become synonymous with the prep culture. If you want to learn more about it, the True Prep and The Official Preppy Handbook are the bible of this culture, written by author Lisa Birnbach. Although a tongue in cheek, they will offer you the much needed glimpse in the old new world, as the author calls it. Stay tuned for our next article and we’ll talk about being prep in more detail.


Share this
Older Post Newer Post