preppy style & clothes primer

The Preppy Style & Clothes Primer

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.

Preppy Groomsmen in Nantucket Reds

Preppy Groomsmen in Nantucket Reds

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.

Preppy Style by the Kiel James Patrick

Preppy Style by the Kiel James Patrick

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.


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 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 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.

Penny Loafers

Penny 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 Hunting Shoes

L.L. Bean Hunting Shoes

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.

Modern preppy style with a Blazer

Modern preppy style with a Blazer

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 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.

Preppy Tie and Bowtie Collection

Preppy Tie and Bowtie Collection

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.


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.


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

Gameday Blazers
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)

More Preppy Resources

Preppy Style by Maddie Rhodes Vickers

Preppy Style by Maddie Rhodes Vickers

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

True Prep and The Official Preppy Handbook – Online blog all about prep culture and Ivy style. – Online blog all about prep culture. – One of the best of its kind, a great blog about preppy culture. – A blog all about classic prep culture. – 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


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!

The Preppy Style & Clothes Primer
Article Name
The Preppy Style & Clothes Primer
All you need to know about the basics of Preppy style, so you can create your own prep look and Ivy League Lifestyle. Brands and items
52 replies
  1. Heinz-Ulrich von Boffke says:

    Very interesting, and it describes my own Mid-Atlantic/Southern family almost to a T, although none of this was ever talked about, labelled, or consciously attempted. It was just how/what we were and to some lesser extent remain.

    Best Regards,

    Heinz-Ulrich von B.

  2. Heinz-Ulrich von Boffke says:

    Forgot to mention that I’m wearing my standard summer (non-teaching) uniform ass I tyoe this reply: shortsleeve Madras shirt, khaki shorts, and leather dock-sider shoes. Long may they live!

    Best Regards,

    Heinz-Ulrich von B.

  3. Herr Doktor says:

    Nice article. I think there are certain hallmarks of style that encompasses both ‘Prep’ and ‘Traditional’. To wit: Quality, Economy and Thrift, and Good Taste. I tend to think Economy and Thrift are leaned-on more heavily in ‘Trad’ and ‘Prep’ relies on a lot of bells and whistles. ‘Brands’, I think are also less important to traditionalists. Hey, I’m simple guy; I could be wrong, but even Lisa Birnbaum said, ‘Prep clothes make sense. Winter clothes keep you warm and rain clothes keep you dry, collars are buttoned down so they don’t flap in your face during Polo.’

  4. Christiaan van Hasselt says:

    Preppy style was, is and remains the standard and the starting point for gentlemen to dress. “hey hey, my my, rock & roll will never die’, Neil Young might as well be singing about preppy style. Luckily he wasn’t and his music is the better for it.

  5. Evan S. says:

    An interesting article. Attending a small private school in The Berkshires (MA) and spending time on the Cape, I see many kids embracing the preppy lifestyle. I have introduced elements into my own style, but would not consider myself preppy. The functionality and history of many of the designs appeal to me because I am an avid outdoorsman, but I just can’t overcome my aversion to dressing in pastel colors.
    -Evan S.

  6. benjaminblue says:

    Thanks for this interesting look at the clothes, the manner and the enduring way of life so emblematic of this subculture. Always — in part, thanks to F. Scott Fitzgerald and despite changes that have occurred in the past few decades — Brooks Brothers, as you said, will remain the epitome of this style. And gin-and-tonics remain the civilized drink of choice. Perhaps, though, you meant to suggest Katharine Hepburn, rather than Audrey Hepburn, when identifying some notable proponents of the preppy style.

    • MarkinTx says:

      Katherine Hepburn is definitely prep both in style and background, but Audrey Hepburn is also commonly called prep in style, mostly owing to her style in Breakfast at Tiffany’s.

  7. Jospar says:

    Excellent article , as I’m in the arse end of mallorca I’m missing the things that unite brits and Americans, but getting in touch with the trash that unites chavs and yanks.

  8. David says:

    I was born and raised on the East Coast to Ivy-league parents who attended Cornell. When, several years back, I started returning to my roots and with that the clothing, you can imagine my surprise at finding out there was a whole movement entitled “Trad,” that seeks to emulate the look I grew up with! Even more amazing is that this apparently was/is a big thing in, of all places Japan, and spread back to the U.S. And finally, that a brilliant designer, who is neither Ivy nor WASP, Ralph Lauren, has made an absolute fortune selling 1950’s and 1960’s East Coast WASP style to the world!

    You may be familiar with message boards where there is an entire forum dedicated to “Trad.” My opinion of the people on it and their clothes, having grown up with this and never giving it much thought, is:
    1) these are people who never grew up with this
    2) many of the outfits are exaggerations to the point of caricatures; endless obsessing about what is or is not “real Trad”
    I must confess to being equal parts amused and annoyed by what I see on “Trad” fora. In recent years, I rarely visit fora of any sort; your pieces I receive happily via direct e-mail.

    Well, enough of my rant. Great piece on the Preppy look!

  9. Ahmed Sajeel says:

    Fantastic. Love it as my own personal style is a hybrid of Agnelli-meets-East Coast Prep. Like I said. Loved it

  10. Guy Graff says:

    I must mention a haberdasher who died back in the early 90’s. His name is/was Shep Miller. His shop of the same name was in Southampeon, NY on the corner of Job’s La and Main St.

    He had the very top clientele in addition to offering wonderful resort clothing. You mentioned colorful clothing in this article which prompted this response, but there was no mention of Shep. Shep traveled to the Ivy League selling his goods early in his career and as I understand it was “the inovator” in offering colorful mens wear. His shop offered the most unique mens clothing in wild colors.

    I purchased summer slacks in yellow silk……………also in pink and wine silk. Also the most beatuful striped polo style shirts in wonderful stripes that are as light as a feather made of Egyptian cotton.

    The list of what he had to offer was long and incredibly wonderful. Thankfully we still have a few shops in NYC to this day that are unique, but they are slowly disappearing.

  11. Gernot_Freiherr_von_Donnerbalken says:

    At first, I’d like to express my thanks for another well written article of this fine gazette. It’s always a pleasure to read in it, and so it has been reading this one.
    I must then express my homage to the preppy style. It really is the best thing that American culture has ever given to the world. There is certainly no style that may be so casual and utterly confortable without being sloppy. And where would my wardrobe be without the versatility of OCBDs, Chinos, and Blazers ? So, here are my thanks and greetings from across the Atlantic.

  12. FrankDrakman says:

    “Prep” is short for “preparatory” school, and refers to the high schools that traditionally fed the Ivies, like Andover/St. Alban’s, etc. At a prep school, you had to wear a blazer, oxford cloth shirts were preferred because they breathed more – important when you’re a teenage boy running from class to class – , loafers were preferred because you could quickly slip them on and off if playing basketball at lunch, rep ties were the norm at these schools (and had their own code – stripe colours might indicate house, achievements, or other status), and &c.

    “Prep wannabee” is the style presented by Ralph Lauren, Hilfiger, and others, who want to give their buyers the look of a class to which they do not belong, as evinced by the author’s note that “prep” includes ” the etiquette and the ethics” which these wannabees have never embraced.

    Two things exemplify true prep: utility, and lack of brand ostentation. A true prep would be horrified by the new generation of Lauren shirts, with “POLO” in foot high letters on the chest. Preps wore casual cotton shirts where the biggest logo might be the Lacoste Crocodile, or the Munsingwear penguin. These shirts were made of heavy cotton, and had to stand up to activity, sweat, salt, and sun for years (utility) while retaining their shape (colour could, of course, fade gracefully). Bean duck shoes may not look fashionable, but they keep your feet dry and don’t stain from the winter or ocean salt. No prep would be caught dead with a Louis Vuitton overnight bag; he’d have an old canvas or leather bag he’s had since high school, and while worn-looking, is still serviceable. Utility ultimately means paying less because buying good quality means your gear will last.

    Another element of utility was timelessness. A blue blazer with grey flannels is appropriate for all but the most formal occasions; a blazer with chinos is delightfully dressy in a casual setting. Preps don’t worry about ‘fashion’ – what colour/ what length/ what stripe is “in” this year – they buy what works, and keep (and wear) it for years. Preps don’t care about contrasting shirt collars, or collar bars; they buy plain or button downs. They don’t look for ‘slim’ or ‘tailored’ fit; they buy relaxed fit because they are, above all, relaxed. And that’s the real point.

    The true differentiator between the prep and the prep wannabee is attitude. The wannabee is striving, desperate to be included, mocking preps by imitating their dress and style (however brazenly and poorly), whilst grasping nothing of the underlying ethos. The prep is relaxed, genial, accommodating, generous, and, for lack of a better term, ‘classy’. The casual good manners of the prep are unforced and unthought; the mannerisms of the wannabee are calculated and hungry. Dressing wannabees in prep-like clothing is akin to the old proverb of applying lipstick to sows.

    • Gernot_Freiherr_von_Donnerbalken says:

      The opposition of wannabees and “true” ones is a timeless one that has been reflected by art for ages. No one of the readers will disagree that pretenciousness and “overdoing it” don’t make for style. From Titus Petronicus’ ” Satyricon to Molière’s “Le Bourgeois Gentilhomme” pretenciousness has always been ridiculed, and that rightly.
      Ralph Lauren is really a most unfortunate case, as their “Big Pony Collection” certainly doesn’t reflect understatement nor style and now only serve as a bragging item for partying law students. It is most lamentable that there are such perversions. I might say, though, that I am optimistic enough to believe that readers of this fine Gazette would instinctively refrain from such.

    • Brett says:

      As a person who cut my teeth at a Prep School in Connecticut, I could not have said it better myself!
      Only a sturdy, OCBD could have taken the abuse of impromptu football games or snowball fights on the Commons, then been stuffed in a mesh bag to be washed in the commercial – style laundry. The blue blazer helped conceal the wrinkles from that same shirt after being balled up in the corner of the locker room during hockey practice. And the frayed hem and slight grass stains barely showed on the gray or khaki trousers. Utilitarian and classy. And when you start off your formative years that way, you always realize comfort does not mean ripped jeans and a t-shirt, and getting dressed up has nothing to do with fashion.

      • William Quick says:

        Hill School old boy here, and yep. Our laundry was hidden away beneath the gym, and occasionally ate my shirts.

        I never thought of this as a style. It was just the way I, and everybody I knew, dressed. We didn’t really have to think about it. Fifty years later, I still dress that way, and I still don’t think much about it. Some things look and feel right, and I wear them. Others don’t, and I don’t.

        Half the things in my closet are at least a quarter century old. And some are much older.

        I find it fascinating that some people seem to get so worked up over a subject I still find somewhat mundane. It’s just clothes, after all.

    • Rosie says:

      I think your blurb is a little unkind to those you label ‘wannabes’. You may not know that ‘imitation is the sincerest form of flattery’. Yes to the remarks on utility – top quality, plain, serviceable and last for years is what the upper classes look for. But no real Sloane would ever use the term ‘classy’. Prep is the US’s best effort at aping the English upper classes, and while it has some attractive aspects, falls way short overall.

      • MarkinTx says:

        You started off chiding him for perceived snobbery, and then exemplified Anglophilic snobbery yourself: “Prep is the US’s best effort at aping the English upper classes, and while it has some attractive aspects, falls way short overall.” As well, you were factually wrong. Prep doesn’t “ape” the English upper classes, if you knew the history, you’d know there was a healthy amount of cross-germination between the cultures of the Northeastern elites and the English upper classes in the late 19th through pre-war period, with a lot of emulation by both sides.

    • MarkinTx says:

      Frank, you hit the nail on the head. I’m 40, grew up a prep here on the Texas coast (anyone doubting that Texas can be prep – consider that even debutantes up in the Northeast do the “Texas dip”). I did go public school, but in a wealthy part of town, had my tennis lessons at the country club, then went to SMU (mentioned in the OPH), was on the sailing team, in a fraternity. I remember when the first preppy craze emerged in the early 80s, I had my little Lacoste shirts and Sperry Topsiders, but I remember something else – the prices were much lower on these prestige brands. My parents were well-off, but they weren’t spendthrifts (my dad is Quaker and always hated ostentation). A pair of Sperry AOs today is $95 and a Lacoste L.12.12. polo is $90 – my mother would have never spent that much in equivalent 1980s dollars to outfit three growing boys. Back then, the prestige seemed to be related to a genuine association with a particular outdoorsy leisure lifestyle; the Lacoste shirt was genuinely created to make tennis playing more comfortable, the Sperry to make sailing safer, so these brands had earned their prestige through authenticity, and then maybe come to command higher prices than your typical JC Penny clothing because of desirability. That’s not the case for the newer crop of preppy prestige brands like Vineyard Vines, and all the overdone “Southerns” (Southern Marsh, Southern Tide, Southern Proper). Instead of modestly trying to genuinely help people do their outdoor leisure activities better, the new brands decide from the start they are going to introduce their brand at a prestige-level price point, and then create a very contrived and artificial aspirational story behind their brand. It’s very cynical and crass, very ostentatious and materialist, not at all genuine prep. But the new generation of prep wannabes lap it up, the latest brand to release its polo shirts (which cost $3 a piece in a 3rd World sweatshop) for $70 with a catchy logo and stores reminiscent of a coastal boutique, it flies off the shelves and is immediately seen all over the place, on people who have never once done any of the outdoor leisure activities the brand purports to embody.

  13. R. Folger says:

    One of the things I find most peculiar about the recent popularization of “preppy” is that its most vocal proponents aren’t from the background they covet (or in some cases, the background they claim). Christian Chensvold isn’t a “real preppy”, although his blog often has interesting historical stuff, and at least he uses his real name and gives full disclosure about his background. Kiel James Patrick (born Kiel James McKivergan) was anything but preppy until a few years ago; likewise, Fred Castleberry. Even “Muffy Aldrich” of the Daily Prep is dubious; her real name is Lisa Wezniak and her background is much less patrician than she pretends it is.

    In building ersatz preppy personae, these bloggers aspire to be accepted as the real thing. But aspiring to appear to be anything different from what one was born into, is deeply un-preppy. People who grew up in that world tend to be diffident about it (often even apologetic), and the thought of parading their backgrounds as “lifestyle” for public consumption is anathema. Other than a few career choices (such as going into politics, like GHW Bush, or being a public intellectual like WF Buckley) most truly preppy people shun the limelight, just as their parents taught them to do. It’s all part of the Puritan ethic that has been at the core of the east coast WASP establishment over the past four centuries; something that’s been entirely missed by “preppy” bloggers.

    • Sven Raphael Schneider says:

      Nobody can choose who they are born to, or who their parents are, but one can choose one’s interests and hobbies. Likewise, everyone can create a website, write a blog or take pictures. Of course, it is a bit strange if people change their names to sound a bit more preppy but at the end of the day, it’s their business.
      Background is one thing, achievements another. If no real preppy person wants to discuss the style online, but there is a general interest, I don’t see why it’s a bad thing to see others write about it as long as it is substantiated and not made up. At the same time, nobody forces you to read their stuff and you can freely express your opinion – isn’t it nice to live in such a free world?
      Bear in mind, ti’s always easier to criticize than to create something.

      • R. Folger says:

        I never suggested that people shouldn’t make a website and say whatever they wanted, within the limits of the law and their stomach for public embarrassment; I merely said it was “peculiar”. Having said that, there are two conditions to presenting an image to the public that I think are sensible. First, if someone sets themselves up as an authority on a subject, or even accepts others claiming they’re an authority, but they’re demonstrably not an authority, they run the risk of being called on it, if . Second, if there are contradictions in their claims (such as their background), they should be prepared for others to call them on those.

        If a German prince ran a blog on European nobility and aristocracy, and portrayed himself as a specimen of the type (which, of course, goes far beyond mere clothing and other trappings, to noblesse oblige, land, duty, mores, etc.), the public might be willing to accept his claims. If it turned out that, rather than being a prince, he was formerly a butcher and now runs a string of brothels, we might rightly feel like he was a fraud. Such is the case with “Marcus Prinz von Anhalt”, who also calls himself “Prince Germany”. Born Marcus Eberhardt, when he was 40, he paid millions to have himself “adopted” by another charlatan, in order to have the legal surname “Prinz von Anhalt”, to give the impression that he’s a real prince.

        It’s not so different in the US, in that the background known as “preppy” is a manifestation of the closest thing we have to an aristocracy (or at least a gentry). The clothing and accessories, cars, alma matres and other trappings are the superficial aspect of it, but there is a deeper part of it that is being done an injustice by some of the current poseurs. The subculture they are aping (New England old WASP establishiment) have always been far more about hewing to the values and traditions of their parents and grandparents, to understatement and modesty, to public service and charity, to thrift and so on, than they ever were to wearing pink and green or drinking G&Ts.

        If people who have some of the superficial aspects but few of the deeper qualities are allowed to commandeer the public face of the subculture without being challenged, it will hammer one more nail in the coffin of American high culture. That may not bother some, but given that this group contributed more to the foundation and rise of America than any other, perhaps it ought to.

        • Sven Raphael Schneider says:

          I never said you did ;). In Germany Prinz is a part of your name and not a formal title, just like von… I agree with you though that it is important to look at things or people as a whole because drinking wine, preaching water is never admirable. That being said, it seems to me that none of the bloggers should be compared to Mrs. Gabor’s husband. Did you do some research on their background?
          Considering that you mention the preppy ethics and values, it seems surprising to me, that bloggers in this segment seem to be critiqued so harshly – just remember the WASP101 thing. What the blogger did was shameful, but the reactions were just as bad. In my opinion, that discussion reflected very poorly on anyone involved.

          • Michael R says:

            Sven, beautifully said. The low-level bitchery in R. Folger’s comments are depressing. Everyone fancies themselves an amateur sleuth on blogs like these. While they’re busy showing off their Internet searching acumen, all they do is reveal themselves to be beetle-browed fetishists of a different sort.

  14. Michael says:

    How could you miss Lacoste in the list of preppy brands?! Iconic preppiness ……. I’m still in shock

    • Leon says:

      Maybe because Lacoste has been deteriorating for at least two decades now. I own a 25+ year old Lacoste Polo, made in France – it is virtually indestructible. New Lacoste stuff is not nearly as robust, it’s just overpriced (imho). Plus the brand has been watered down – their business model is to license out the crocodile-logo so it is being put on all kinds of things (of sometimes questionable design).

      • William Quick says:

        Agree on the new Lacoste stuff. Terrible, compared to the old that I wore at school, long before Lauren ever hove onto the scene. I still wish I had a few of those shirts, but even they wore out. Eventually.

  15. Jack O says:

    Hi Sven,
    Love the article, you’ll find that the preppy look its pretty well established down here in Melbourne.
    What did catch my eye were the Pale yellow trousers with the nautical flag/Anchor emblem on them, any idea where I could find those? I’ve been searching the net for days looking for them.


  16. Guy Graff says:

    The term “Prep” or “Preppy” is a description of those who attended preparatory schools usually located in the Northeast. They are prepared in the prep schools to enter the Ivy League universities. Going back some years ago, a Southampton, LI haberdasher, Shep Miller, traveled to prep schools and Ivy League Universities selling the styles associated with the preppy. In fact, Shep invented the men’s resort style of bold colors which he sold to Wall St and Hollywood types among others in the Hampton’s.

Trackbacks & Pingbacks

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  3. […] television shows like Saved by the Bell and movies about wealthy country clubs began showing the Preppy, Ivy and Trad styles to those outside the Northeastern United States. Companies like Brooks […]

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  6. […] by Lisa Birnbach the boat shoe began to be identified as an essential and integral part of the Preppy style. Boat shoes, however, are not just restricted to preppies but have been adopted by a large […]

  7. […] in a way that makes it difficult to differentiate them from one another.We’ve discussed preppy style in detail and in this primer, we’re going to focus on the Ivy style, which unbeknownst to […]

  8. […] well-to-do to engage in sport and socialize at the same time. With the birth of Ivy Style, Trad and Prepdom, it emerged as one of the most stylish sports for the modern […]

  9. […] the Trad, Ivy League and preppy styles of the 1950s and 60s gained popularity across the United States, Bill St. John began to launch his […]

  10. […] Brown and Cornell. Although the book was published exclusively in Japanese, collectors and Preppy Style enthusiasts were willing to spend an excessive amount of money (sometimes up to $2000) for a […]

  11. […] ‘H’ to the front of its jerseys and the ‘V’ necked letter cardigan became a prep favorite on campuses across the […]

  12. […] by Lisa Birnbach the boat shoe began to be identified as an essential and integral part of the Preppy style. Boat shoes however are not just restricted to preppies but have been adopted by a large […]

  13. […] to become the next great thing to happen to our incredible and vibrant ivy styled, perfectly prep culture of beach bonfires and spring garden […]

  14. […] style is often considered to be influenced by the 20’s and 30’s American collegiate prep style, and his use of a scarf or an old tie as a substitute for a belt reflects this. Long after his […]

  15. […] by Tom Jones that had pink and mint green cuffs. As a teenager he neared obsession with the wasp / prep style and learned to appreciate the beauty of architecture and design. One day in 1977, he stumbled upon […]

  16. […] is a new blog that focuses on everything preppy or related to the Ivy-League Style. You can find a lot of pictures there from various decades, […]

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  18. […] and the G9 was picked up by the students of Ivy League colleges and soon became a staple of the preppy look. It was the perfect prep garment, not informal yet still […]

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  20. […] the New World, they brought with them, what is now often characterized as the “typical” prep sport; Rowing. When the crews from Harvard and Yale met in a challenge race, it quickly became one […]

  21. […] in the Hamptons with your girlfriend. You attended the finest schools, pride yourself on being the ultimate prep and wear boat shoes and anchor bracelets like they’re going out of […]

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