The Preppy Style & Clothes Primer

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Preppy style is largely linked to those who have attended or graduated from Ivy League schools and preparatory academies in the Northeast United States. But while Ivy League schools may be exclusive, Preppy Style isn’t–and remains a wonderful subset of classic style that’s available to anyone who’s interested!

Late for Class? Catch Up on the Preppy Aesthetic with Our Video Guide

Caught at a late lunch at the yacht club? Waiting in line to get your ginghams pressed? Why not pass the time with Raphael who will take you through the essentials of the preppy look, its history, and how you can add some collegiate flair to your wardrobe.

What Does “Preppy Style” Mean? Old (Ivy League) Money!

Traditionally the terms “prep,” “preppy,” “prepster” or any other variation were historically used to describe a subculture of the upper-class youth born into old money in the Northeastern United States. They would attend their family’s 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.

Ivy League School Flags
Ivy League School Flags. Image credit: Columbia Alumni Association

As these prestigious halls of education are otherwise known as “preparatory” schools, you can see how the moniker of “prep” and “preppy” style came to be.

Andy Bernard is an Icon of Preppy Style

Andy Bernard: Preppy Icon

Even casual fans of the US version of TV sitcom ‘The Office’ will be aware that the character of Andy Bernard is an Ivy League graduate. A proud alumnus of Cornell University, Andy’s fashion sense is firmly rooted in Preppy Style – although admittedly more intensely portrayed for the sake of the screen!

Is Preppy Style Just for Ivy League Schools?

Today, the term “preppy” is far looser and is regularly used in high schools across North America and parts of Europe. It still accurately describes the subculture of those who have adopted a manner of speech, vocabulary, dress, manners, and etiquette which is reflective of the traditions adopted from those historic upper-class Northeastern families.

Nowadays, the prep style is far more accessible to a greater range of people. Just as many other elements of fashion originating in wealthier wardrobes, preppy style icons such as salmon-pink trousers, cable knit sweaters, and the humble button-down shirt have all become more affordable to a greater range of classic style enthusiasts.

F.E. Castleberry of Unabashedly Prep wearing a varsity jacket, ocbd, rugby shirt, green chinos, and tassel loafers without socks

Preppy Style in a Nutshell

Almost like a 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 similar brands. Colors and patterns may be mixed, too, and the overall feel is that of a more relaxed formality without being too casual. One relatively telltale sign of a prep is this very particular sense of the style adopted by the average preppy.

An Introduction to Prep Style

Taking inspiration from the Ivy League styles of the past and the nautical flair of many East Coast villages, prep style enjoys a quiet evolution, with much of the style’s backbone remaining the same since the mid 1980s. Naturally, this includes style staples such as bow ties, boat shoes, madras, and other such garments that showcase the styles of some of America’s most established and iconic haberdasheries.

The Official Preppy Handbook Started Out As a Parody

One way to explain the culture is to compare it to dandyism. Lisa Birnbach’s books ‘The Official Preppy Handbook’ and ‘True Prep’ act as great further reading that will give you deeper knowledge behind what it means to be a prep.

The Official Preppy Handbook originally started life as a parody
The Official Preppy Handbook originally started life as a parody. Image credit: The New York Times

What is interesting, however, is that when Birnbach wrote The Official Preppy Handbook, 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, thus increasing the spread and awareness of prep culture and style throughout the world.

History of Preppy Style

J. Press & Brooks Brothers Kickstart Preppy Style

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 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.

Preppy Style Becomes Perfect Leisure Wear

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.

J C Leyendecker captures a preppy golfer

Sporting Influences

With the popularity of traditional New England sporting 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 was influenced by these activities, it stood to reason that students on campus began wearing the clothing to those respective events, matches, and games.

Preppy Style Grows in the 60s and 70s

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 rising interest of the bold and colorful clothing well known for being worn throughout the 1960s and 70s.

In the realm of menswear, 1967 marked the release of arguably one of the most influential films when it comes to preppy style; The Graduate. Starring Dustin Hoffman as recent college graduate Benjamin Braddock, the film features many preppy style staples throughout the film. Admittedly not as bright or daring as preppy style can be, The Graduate showcases seersucker, knit ties, button-down shirts, and corduroy jackets in an undeniably preppy aesthetic.

The 1980s Solidifies Preppy Style’s Staying Power

By the 1980s, preppy style was in a class of its own with dozens of companies opening up shops to cater to a wealthy clientele who treated clothing and the cultivation of a particular image with a passion hardly seen in America before.

A vintage Ralph Lauren advertisement shoes the infamous preppy combo of pink and green
A vintage Ralph Lauren advertisement shows the infamous preppy combo of pink and green. Image credit: eBay

Top designers in the mid-1980s began to catch on to this trend and started designing professional wear for women in New York who had developed a love for the prep subculture when they were Ivy-League students. Classic attire such as tailored skirts, suits, and dresses began to adopt nautical and equestrian elements with pops of pastel colors.

Preppy Style FAQs

Is preppy still in style?

Although some decades have leaned into preppy style more than others, preppy style is often considered a timeless facet of the overall classic style aesthetic.

What is a preppy man?

A preppy man will likely refer to someone who embodies both the aesthetic and lifestyle of prep culture. This may include either having been educated at an Ivy League school, or simply being an enthusiastic onlooker of the preppy culture, lifestyle, and look.

What do preppy guys wear?

Preppy styles can include a range of specific items, fabrics, and details. Seersucker, linen, Madras, tweed, and waxed cotton make up the majority of the materials used in preppy clothing. Meanwhile, OCBD shirts, polo shirts, khakis and chinos, navy blazers, and tweed jackets are some of the preppy style staples.

What does it mean if someone calls you preppy?

If someone should call you preppy, this is likely a compliment, but it could also be construed as a slight – depending on the context, of course! In this day and age, being called preppy is typically a reflection of your outfit(s), and adherence to the preppy style.

What year is preppy?

While preppy style originated at the turn of the 20th Century and has existed throughout the Golden Age of classic style, preppy style had its strongest boom in the 1980s. This era still influences how preppy style is perceived and presented today.

What do preppy people wear?

Preppy people will wear a range of clothing styles, but most notable items include navy blazers, seersucker, and tweed suits, button-down shirts, polo shirts, and rugby shirts, cable knit and tennis sweaters, chinos and Nantucket red pants, Madras checks, and a range of classic accessories including repp stripe neckties and bowties.

Is preppy timeless?

In a word: Yes – preppy style is timeless! It’s a facet of classic style that has been around since the early 1900s and has endured for many years since.

Preppy Clothing Essentials

If you’re looking to create or expand a preppy wardrobe, these are the top must-have items you can search for. While a lot of retailers will likely offer versions of preppy style staples, you’ll likely find some of the best things are found in thrift or second-hand stores, listed on eBay or Etsy, or at estate sales.

Preppy Style Jackets and Blazers

Preston in a double-breasted navy blazer
Preston in a double-breasted navy 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. But, you can always go for the double-breasted look for an increased nautical feel. Of course, many companies make these blazers but the most popular today seem to be from Ralph Lauren and Brooks Brothers.

Preppy Style Shirts

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 a regular dress shirt. Using buttons that fasten down the collar points on the front of the shirt meant these 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 can also be referred to as golf or tennis shirts, 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.

Preppy Style Trousers and Pants

Chinos

Chinos are trousers made from 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.

GTH (Go To Hell) Pants

GTH pants take some serious getting used to. This is a style of its own and one that will surely net you either looks of disdain or 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.

Nantucket Reds

Nantucket Reds are an essential component of 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.

Preppy Style Knitwear

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.

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.

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.

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.

Preppy Style Footwear

Boat Shoes

Like many staples in prep style, you either love boat shoes or hate them. 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 made of leather but can be crafted from other materials such as canvas. They are typically worn without socks as a casual shoe, and as such are tied using leather boat shoelaces.

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.

Photo of white bucks worn with seersucker
Raphael white bucks blue socks with clocks red shoelaces Fort Belvedere

White Shoes

White buckskin shoes aka white bucks are a popular preppy companion to seersucker pants, 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 the front side of buckskin leather can be very nice as well. Many white bucks come with a lightweight, red rubber sole although they can also be found with classic leather soles in the Goodyear construction.

Preppy Style Outerwear

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 with an extra game pocket, and the Bedale, which was made for horseback riding. Either of these options in either classic navy or olive green will work for you within your preppy wardrobe.

Quilted tweed jacket with burgundy suede gloves
Quilted tweed jacket with burgundy suede gloves

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.

Preppy Style Accessories

Anchor Bracelets

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

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

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.

A group of preppy belts
A group of preppy belts

D-ring or Ribbon Belts

Traditionally called a “Ribbon Belt,” 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.

D Ring belts are a mainstay of the preppy style
D Ring belts are a mainstay of the preppy style. Image credit: Belted Cow Company

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 fabrics and materials from sailing cloth to fine cordovan leathers.

Ties & Bowties

Although not exclusive to prep style, you’re bound to see more repp stripe neckties and bow ties as part of this aesthetic. Resembling the collegiate stripes and crests, bold striped neckwear is a must here, but you can also focus on more professorial selections including warm colors and small patterns for a quieter take on preppy neckwear.

Even More Preppy Style Essentials

Madras

Madras is also a cotton fabric that is generally very lightweight and features a textured plaid design. Aside from pants, you can also find many pairs of shorts and jackets made of it. The Madras pattern is available in regular cotton and seersucker as well as patchwork madras consisting of several different pieces of Madras cloth being sewn together. This is very popular in the prep culture and something widely used by Brooks Brothers, among other fine haberdashers that focus on prep style.

Seersucker

Seersucker is another iconic fabric used in prep style. 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.

Raphael wearing a seersucker suit and white brogues
Sven Raphael Schneider, in a seersucker suit and white brogues, knows that style knows no age

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 fantastic to wear in the hot summer months – especially if you need to wear suits at work.

Sporting Leisurewear

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. Think of classic leisurewear from activities such as golf, tennis, cricket, rugby, sailing, and equestrian apparel.

Tweed

During fall and winter, a true prep can rarely be seen without any form of tweed. Certainly a sure fire way to enliven a preppy outfit in cooler months, tweed in any capacity is a welcome addition to a prep’s wardrobe. Instead of giving you all kinds of tweed advice here, head over to our ultimate tweed guide and enjoy.

Four men seated at a bench with a fifth standing behind all wearing suits
Preppy Style in abundance!

Now that you know how
to be preppy, learn more
about the Ivy Look!

Are you a devotee of the Preppy look, or do you prefer a different take on classic style? Let us know in the comments!

Reader Comments

  1. 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. 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. 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. 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. 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. 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.

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

  10. 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. 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. “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.

    1. 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.

    2. 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.

      1. 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.

    3. 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.

      1. 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.

    4. 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.

    5. Most people are unaware that Lauren’s first job of any consequence was at Brooks. His first Polo button-down shirt was a knock-off of the Brooks. Growing up in Florida we used to always joke that if you lost your sale you take off your Brooks shirt and use it to get into port!

  13. 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.

    1. 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.

      1. 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.

        1. 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.

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

    1. 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).

      1. 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. 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.

    Thanks,
    Jack

  16. 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.

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