Preppy Outfit Ideas – Class in Your Wardrobe

Preppy Outfit Ideas

Preppy is an American style that never goes out of fashion. It has enchanted wearers and designers alike. When it originated, it belonged to only a few high-class young people. But with some popular designers such as Perry Ellis, Arthur Cinader, Marc Jacobs, to more recently Jena Lyons and Michael Kors, to name a few, many designers have experimented and showcased their preppy outfit ideas to the world. Designing houses such as J. Crew and Tommy Hilfiger made preppy outfits available to the masses. As a result, it is not only the fashion game of a handful anymore. This blog post is dedicated to this subculture and the birth of a style that has ruled many a heart and runways too.

What does preppy mean?

According to leading dictionaries, preppy means a student of an expensive prep school. Going by this definition, any person resembling such a student in appearance or attire is also called preppy. Derived from this definition, ‘preppy’ is also used as an adjective, which means neat and expensive. So, a ‘preppy look’ means a ‘neat and expensive look’. Therefore, preppy outfits usually refer to attires that look plain and formal, but expensive. A lot of celebrities sport such preppy outfits these days. So, followers and commoners also look for preppy outfit ideas to match the styles of their favorite celebrities.

Preppy Culture – The Origin of Preppy Outfit Ideas

Preppy Outfit Ideas
Image Credit: Ian Drummond Vintage

The preppy culture originated from a subculture in the United States, particularly that of Northeastern college preparatory schools in the early to the mid-20th century. One of the main goals of such prep schools was to groom children for Ivy League universities. The Ivy League institutes are some of the most distinguished ones such as Harvard, Princeton, Brown, Columbia, Yale, and Dartmouth Universities, to name a few.

Children of affluent families used to go to expensive prep schools. These preparatory schools were inspired by conventional English dress codes and uniforms in plaid prints and monochromatic colors. After graduating from the prep schools and the universities, the alumni continued wearing these clothes. This was mainly because these clothes looked classy and upper-class, matching the refined taste of these rich kids. This led to the preppy culture. Not just the dressing style, the preppy culture also included speech, etiquette, and mannerisms that reflected the upper-class and upper-middle-class upbringing.

What is Preppy Style?

The preppy style is a trend that started in the 1920s and then kept evolving over the last few decades. It is still quite prevalent and sought-after in urban and semi-urban areas in different countries. This is mainly adopted by rich people and celebrities. Due to their exclusive look and how the celebrities don them, followers and common people also copy their styles to appear more upmarket. Basically, it is a plain yet chic look. This look is inspired by the preppy culture that originated in the Northeastern part of the United States. When we say preppy outfit ideas, we think more about structured silhouettes, plaid prints, nautical stripes, refined jewelry, and pastel color garments.

Preppy culture has inspired many designers and is still doing so. Starting from the very famous Arthur Cinader (founder of the J.Crew apparel store) to more recently Emili Sindlev and Tamu McPherson – every designer has experimented with preppy outfits. Even in 2023, various designers launched their own preppy outfit ideas on the runways. It also motivated more people to adopt the nuances of a preppy lifestyle to look ‘neat, attractive and classy’.

Preppy Outfit Ideas for Men

Preppy Outfit Ideas
Image Credit: Ivy League Style

The inspiration for preppy fashion for men was primarily drawn from the ‘Ivy’ Style of dress around 1950. This is based on the kind of clothing men used to wear while indulging in sports like polo, golf, squash, and tennis, to name a few – mostly sports enjoyed by the upper classes in England. Therefore, it draws heavily from British country clothing such as tweed sports coats, polo tops, waist coats, trousers, flannels, regular T-Shirts, collared T-Shirts, jumpers, boat shoes, and brogue shoes.

Eventually, the preppy outfit ideas for men became more casual. Brands such as Lacoste, Ralph Lauren, Daniel Crémieux, and Izod brought more youthfulness to preppy fashion for men. More fashion designers got interested in preppy fashion for men. They brought in their preppy outfit ideas and experimented with braces, badges, and checked patterns.

Preppy Outfit Ideas for Women

preppy aesthetics

While preppy fashion started off earlier for men, it was in the 1960s when the preppy fashion for women emerged. Some of the famous designers of those days, who trailblazed into this subversive fashion were Perry Ellis, Oleg Cassini, and Lily Pulitzer. Some popular fashions based on preppy were – twin sets or cropped sweaters thrown over collared shirts, plaid printed skirts, sexy pin-up styles, pencil skirts, tailored skirt suits, and low heels. They completed the look with heavy foundation, light eyeshadow, red or pink lips, and soft pastel pink blush.

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But as fashion keeps evolving with time, so did preppy outfit ideas for women. More designers brought their adaptations of preppy fashion. Some well-known designers who made preppy fashion more fun and available to the masses are Ralph Lauren, Tommy Hilfiger, Gant, J.Crew, Vineyard Vines, and Elizabeth McKay.

Preppy Outfit Ideas in the 80s

preppy aesthetic

By the 80s, preppy fashion was no longer only for the privileged classes. Thanks to new-age designers, especially Ralph Lauren and Tommy Hilfiger, preppy fashion was more accessible to the masses. The rich were still abiding by it. And the middle class also adopted this subcultural fashion as a part of regular wear or work wear. Princess Diana and Brooke Shields spearheaded the 80s-style preppy outfit ideas.

Some preppy outfit ideas included sweaters, blazers, casual button-down shirts, loafers, polo shirts, boat shoes, and silk knit neckties. People were experimenting with different materials and designs such as seersuckers, grosgrain, madras clothing, and tartan designs. With the financial backing of Mohan Murjani, an Indian textile business tycoon, Tommy Hilfiger debuted his signature collection, which comprised preppy clothing for men. With this, he further modernized the button-down shirts and chinos, thereby bringing a more casual attitude and youthfulness to preppy outfit ideas for men.

Preppy Outfit Ideas in the 90s

preppy style inspiration
Preppy Meets Grunge

The Ivy-League style preppy outfit ideas segued from the 80s to the 90s with new and riveting twists when preppy met grunge. Plaid oversized shirts de-emphasizing the silhouette paired with boot-cut jeans, and loose argyle sweaters paired with short pleated skirts were in. The 90s also saw oversized plaid or patterned blazers thrown over cycling shorts and crop tops. The torchbearers of this amalgamation between preppy and grunge were designer Marc Jacobs, design house J. Crew, and American clothing brand Tommy Hilfiger.

Preppy Outfit Ideas in the 2000s

preppy dresses pinterest

With the turn of the millennium, preppy outfit ideas also got a fresh new appeal. Preppy became more colorful and full of sparkles, and playful patterns emerged from leading design houses such as J. Crew. However, soon there was a new twist in preppy fashion as ‘Athleisure’ entered the scene giving preppy outfits another cool twist. Around 2015, we saw apparel stores being dominated by comfy joggers and leggings. The aisles of apparel stores were bearing more black, olive, teal, navy blue, grey, and all the other sporty-colored athleisure.

Preppy Outfit Ideas in 2023

preppy outfit ideas
Image Credit: Getty Images

The spring/summer collection is already headlining many fashion weeks. And prep still has a firm footing with many designers worth their salt. While European houses are inclined towards the “classic” culture. American brands are still making the cut with rugby stripes, wide-cut chinos, vintage Cartier watches, and clothes meant for activities specific to the country club.

The big news is J.Crew is back, and so are men and women thronging the aisles of this flagbearer of prep. Blazers and pencil skirts, crew-neck sweaters, cashmere twin sets, and totes are getting newer twists, clashing contrasts, and heady spins from popular designers. How about a floral print tie on a striped shirt with a yellow leather mini? Thanks to Emily Sindlev for such preppy outfit ideas who even set a baseball cap and retro sneakers to complete the look.

Or how about  old-fashioned preppy vibes by going back to school uniform, albeit with a twist. Popular designer brand Miu Miu (known for their innovative preppy outfit ideas) takes us back to school in their latest spring/ summer 2023 show. In 2022, they had literally cut up everyday pieces – chinos, blue-collar working shirts, knit sweaters, argyle sweaters, and car coats in their collection called ‘Basic Instinct’. This year it was a polo top, knee-length (or mini) skirt worn with white socks and kitten heels.

Why Does Prep Never Go Out of Style?

It is because people understand this fashion. Prep is conservative, yet cool. And you can experiment with it endlessly to make it unusual and exciting. Designers, new and old, feel like going back to their drawing board with preppy outfit ideas. Brands that seem to be shaking the world of fashion, are universally considered preppy. As Ralph Lauren puts it, you can put your own spin on it and make your own formidable personal style.

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Preppy Fashion in Movies

preppy aesthetic
Image Credit: GlamAmor

Fashion and movies have always been hand in hand. While movies draw inspiration from the catwalks, people follow movie star looks. Then it becomes a trend. And this is true for preppy culture also, which is best represented by

  • clothes that are neat, classy, and pricey
  • polished mannerisms and etiquettes of young people
  • refined and rich social circles

This class and its trappings have often been the muse for various characters in countless movies, TV series, and web series like Blair Waldorf in Gossip Girl, Joey, Pacey and the gang in Dawson’s Creek (which inspired a whole catalog at J. Crew), Dead Poets Society, and not to forget the Harry Potter movies.

How to Get the Preppy Look

First thing you must know when you want to look preppy is that minimalism is the key here. Choose basic clothes that have simple necklines, lend a neat look, etc. You can go for structured silhouettes or oversized attire, depending on your mood or the look you want to create. Some of the prints you can choose from are tartan or plaid, argyle, cable knitting, or plain. Girls can experiment with simple, classy jewelry and complete the look with Mary Jane shoes. While boys can opt for boat shoes, moccasin-style or brogue shoes, and tweed sports jackets. Below are some preppy outfit ideas and looks you can take inspiration from and add a personal touch to get the desired look.

Top-to-Toe Preppy Outfit Ideas for You to Try


cute preppy fashion
Image Credit: Gentleman’s Gazette

To start with, choose a collared top, a button-down shirt, or a rugby T-Shirt with a striped pattern. Plaid shirts are also good options to consider. Experiment with badges and playful logos to give it a chill twist.


preppy girl skirts
Image Credit: Cultura Colectiva

A tartan pattern skirt or a tennis skirt is perfect to pair with your top. A plaid wrap skirt or mid-length skirt suit also makes for good preppy outfit ideas.


preppy girl pants

Whether wearing a crop top, a t-shirt, or a preppy sweater, a pair of chinos goes well with almost anything. They are sporty and playful and can be worn at work and outside. The cargo pants were quite a rage back in the 90s. And these multiple-pocket trousers have never gone out of fashion. If you want some casual and fun preppy outfit ideas, take a cue from Bella Hadid’s cargo pants collection and how she styles them.


preppy ideas about sweater
Image Credit: Town & Country Magazine

Another essential of the preppy look is the sweater or the pullover. There are multiple options to choose from… or better, get them all. Argyle patterns, cable knitting, monochrome cashmere vests, or collegiate sweaters – each design looks stylish while adding warmth to your look. Wear them loose or tucked in, or throw them over your shoulders for a casual yet classy look.


preppy style inspiration
Image Credit: TheStreet

To complete the preppy look, girls can try formal Mary Jane shoes or classy white sneakers. Men can add a touch of class with a brogue or boat shoes. To achieve a more casual look moccasin shoes or sneakers work best.


men women style inspiration
Image Credit: Ralph Lauren

Whether with a formal look or with casual attires, neckties look great on anyone giving instant preppy vibes. Whether working from home or back to the office, in business meetings or luncheons with colleagues, neckties make a smooth transition between the formal and the informal look.

Conclusive Insight on Preppy Outfit Ideas

Preppy fashion has evolved over the years. From the simple and clean looks of the 50s to blending with grunge in the 80s to brightly colored clothes in the 2000s – various designers in different eras have brought their preppy outfit ideas to fashion weeks and into our lives. Despite all the modifications over these years, preppy is still dominating our hearts.

Modern-day fashion designers and iconic apparel stores such as Chloé, Michael Kors, Burberry, Versace, Miu Miu, Noah, Bode, Thome Browne, Gucci, Sindlev, Tamu McPherson, and Dior have taken preppy fashion to the next level with their own versions hitting the runway. At the same time, brands such as J. Crew, Urban Outfitters, Everlane, and Tommy Hilfiger are continuing to bring this cool fashion into the wardrobes of common people.

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