The Preppy Style & Clothes Primer

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.

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: 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.

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.

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.

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.

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 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

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.

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 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.

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.

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.

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.

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