Preppy Style: How to Nail the Fashion Aesthetic in 2024


Joanna Elizabeth


Updated March 10, 2024

Preppy Style
Take a closer look at preppy style.

Preppy style has been a dominant force in the fashion world for over a century. It is a timeless aesthetic that has evolved and adapted to different eras and subcultures. From country club style to vintage-inspired, there are plenty of variations. So what is it exactly?

Preppy style is a fashion aesthetic inspired by the Ivy League look, characterized by clean, classic pieces such as polo shirts, blazers, and loafers. It channels a polished, collegiate appearance focusing on traditional patterns, such as plaid and stripes, and a blend of casual and formal elements.

From its origins in American schools to its influence on street style, it inspires designers and fashion lovers alike today.

Preppy Style Origins

Preppy Runway Fashion
Designer Tory Burch has reimagined the aesthetic for modern day. Photo: Ovidiu Hrubaru /

In the late 19th and early 20th centuries, preppy fashion emerged as a status symbol among wealthy students. This exclusive group of individuals, often from old money families, had a distinct way of dressing that reflected their privileged backgrounds and education. The term “preppy” was derived from the word “prep,” short for preparatory school.

Preppy Clothing Essentials

When it comes to building a preppy wardrobe, there are several key pieces that should be on your radar. These classic items form the foundation of the aesthetic and can be mixed and matched to create a variety of stylish outfits. Let’s explore some of the must-have essentials:

1. The Navy Blazer: A Timeless Classic

Blazer Preppy Aesthetic
A navy blazer is one way to channel the style. Photo: REVOLVE

The navy blazer is a quintessential staple that exudes sophistication and versatility. It can be dressed up with a crisp button-down shirt and a skirt for a formal occasion or paired with jeans and a t-shirt for a more casual look. This versatile piece is a must-have in any preppy wardrobe.

2. Polo Shirts: Sporty and Stylish

Polo Shirt Preppy Look
The polo shirt channels a sporty yet chic vibe. Photo: Shopbop

Polo shirts are synonymous with this style. They offer a perfect balance between casual and refined, making them suitable for a variety of occasions. Opt for colors like white, navy, and pastels, and wear them with chinos or shorts for a preppy summer look.

3. Boat Shoes: Nautical Charm

Boat Shoes Preppy Sperry
Channel nautical vibes in the iconic boat shoe. Photo: Sperry

Boat shoes are essential preppy footwear made by brands like Sperry. These shoes are comfortable, versatile, and exude a nautical charm that perfectly complements the aesthetic. Pair them with shorts, denim, or even summer dresses for a relaxed yet polished look.

4. Button-Down Shirts: Crisp Essential

Button Down Shirt Preppy
From casual to formal, the button-down shirt is a wardrobe essential. Photo: J. Crew

Button-down shirts are a cornerstone of preppy fashion. They deliver a clean and polished look that can be dressed up or down depending on the occasion. Opt for classic patterns like stripes or gingham, and pair them with jeans, a tennis skirt, or khaki pants for a timeless outfit.

5. Cable-Knit Sweaters: Cozy and Chic

Cable Knit Sweater
The iconic cable knit sweater is right at home with a preppy look. Photo: REVOLVE

Cable-knit sweaters are another staple of this style. This staple offers a cozy and chic look that is perfect for colder seasons. Layer them over button-down shirts or wear them on their own with jeans or skirts for a perfect preppy ensemble.

6. Trench Coat: Outerwear Elegance

Trench Coat Navy
Wrap up the aesthetic in a belted trench coat. Photo: Shopbop

A trench coat is a versatile outerwear piece that adds a touch of timeless elegance to any outfit. It is a perfect way to transition from spring to fall and can be worn over both casual and formal attire. Opt for a neutral color palette like beige or navy for a fantastic look.

7. Khaki Pants: Classic and Versatile

Khaki Pants
Embrace the trend with khaki pants that can be styled in so many ways. Photo: Banana Republic

Khaki pants are a wardrobe staple that offers an excellent style for both casual and dressier occasions. Pair them with a button-down shirt and a blazer for a polished preppy look, or dress them down with a polo shirt and boat shoes for a more casual vibe.

8. V-Neck Sweater: Sophisticated Layering

V Neck Sweater
Whether layered or solo, a v-neck sweater is a chic choice. Photo: Shopbop

A v-neck sweater is a sophisticated layering piece that adds a touch of refinement to any outfit. It can be worn over a button-down shirt for a classic look or layered under a blazer for a business casual ensemble. Opt for neutral colors like navy, gray, or camel for an enduring appeal.

9. Oxford Shirts: Timeless Elegance

Oxford Shirt
Embrace pastel shades with the Oxford shirt. Photo: Ralph Lauren

Oxford shirts are a preppy essential that will always be in style. These versatile pieces can be dressed up with a blazer or dressed down with jeans or shorts. Opt for colors like white, blue, or pink for a traditional look.

10. Pleated Skirt: Chic Look

Preppy Pleated Skirt
From long to short, the pleated skirt is an essential staple. Photo: Shopbop

A pleated skirt is synonymous with the preppy aesthetic. It’s a chic look that is perfect for different seasons. Pair them with an elegant blouse and cardigan for the ideal look.

Preppy Aesthetic Timeline

Early 20th Century

Sweater Pearls Preppy Style 1940s
A high school student wears a sweater and pearls in 1943. Photo: Esther Bubley, Public domain, via Wikimedia Commons

The preppy aesthetic, which began shaping American fashion in the 1910s, truly found its footing with the advancement of knitwear techniques in the 1920s. This period introduced the iconic sweaters and cable knits that would become synonymous with the look.

As leisure sports like tennis gained popularity, the style adapted, incorporating tennis skirts and sweater vests into women’s fashion. By the mid-1940s, the distinct look had evolved into what was known as the Ivy League style.

Rise in the 1950s

Anne Gwynne Cardigan Sweater 1940s
Anne Gwynne wears a cardigan sweater look in the 1940s. Photo: U.S. Army, Public domain, via Wikimedia Commons

In the 1950s, preppy expanded beyond the confines of elite educational institutions. Styles like iconic twin sets, sweaters worn over collared shirts, and plaid patterns became synonymous with the era.

The preppy look was no longer limited to school kids. it permeated mainstream fashion and became a cultural phenomenon. A pleated skirt paired with a wool sweater stood out for women. 

During this time, the introduction of sporty rugby shirts into the preppy wardrobe added a new dimension to the style. Initially designed for the sport of rugby, these shirts became famous off the field and were embraced by fashion enthusiasts.

Plaid also gained traction as a preppy print, further solidifying its association with the style.

The Craze of the 1980s

Cardigan Pastel Preppy Style 80s
Pastels wear a signature look of the 80s prep look. Photo:

The 1980s marked a pivotal moment in the evolution of the style. The release of “The Official Preppy Handbook” in 1980 fueled a craze that swept the nation. The book, intended to be humorous and ironic, inspired a new generation to embrace the aesthetic.

During the ’80s, this style underwent a transformation, shedding some of its exclusive associations and becoming more accessible to the masses. Designers like Ralph Lauren, L.L. Bean, and Tommy Hilfiger significantly popularized preppy fashion, making it more mainstream and commercially viable.

Khakis, plaid blazers, and sweater-over-shoulders became ubiquitous symbols of the prep trend. Icons like Brooke Shields and Princess Diana embraced the aesthetic, donning turtlenecks and tartan blazers with their own unique flair.

A New Twist in the 1990s

Ralph Lauren 90s Style Prep
Minimalism was an essential of the 90s preppy look. Photo: /

The 1990s brought a new twist to preppy fashion thanks to the rise of brands like Gap and J. Crew. While the 80s was about bold pastels and prints, the 90s brought about more minimalism.

Still, preppy elements such as boat shoes, polo shirts, and cable-knit sweaters remained a constant presence. Pop culture played a significant role in shaping the perception of preppy looks during this decade.

Britney Spears, with her schoolgirl-inspired outfits, became an icon of ’90s preppy fashion. And we must remember Clueless and Alicia Silverstone’s yellow checkered look. Television shows like “Dawson’s Creek” featured characters sporting the looks. 

Reinvented in the 2000s

Jenna Lyons Preppy Style
Former J. Crew president Jenna Lyons helped shape the aesthetic in the 2000s. Photo: Featureflash Photo Agency /

In the early 2000s, preppy took on a new direction, thanks to designers like Jenna Lyons at J.Crew. This era saw a shift towards bright colors, playful twists, and a more fashion-forward approach to preppy fashion. The traditional aesthetic gave way to a more vibrant and eclectic interpretation of the style.

Shows such as Gossip Girl brought the school uniform look into the spotlight. As the decade progressed into the 2010s, this style waned in favor of a more indie aesthetic. 

A Resurgence Today

Modern Preppy Style Plaid Skirt Outfit
Prep style today can be seen in darker colors and new silhouettes. Photo: FP

In recent years, preppy fashion has made a comeback, reclaiming its position as a fashion staple. Fashion Week runways have featured collections that pay homage to preppy aesthetics. From Anna Sui to Versace, tweeds and argyle have made a comeback.

The new era embraces individuality and personal style while still nodding to the traditional elements of preppy fashion.

Classic preppy pieces like the navy blazer, polo shirts, boat shoes, and cable-knit sweaters remain wardrobe staples. The enduring appeal of this look lies in its versatility and timelessness.

Quick Tips

Woman Plaid Skirt Preppy Style
Plaid print is a major staple of the style. Photo: FP

What is preppy style?

Preppy style refers to a fashion aesthetic that originated from the clothing worn by students in prep schools and Ivy League universities in the early 20th century. Clean lines, tailored silhouettes, and a mix of classic and sporty elements characterize it.

What are the key elements of preppy fashion?

The key elements of preppy fashion include polo shirts, button-down Oxford shirts, cable-knit sweaters, blazers, chino pants, A-line skirts, loafers, and accessories like pearl necklaces, headbands, and bow ties.

The color palette typically consists of navy, white, pastels, and classic patterns like stripes, plaids, and argyle.

How can I incorporate the preppy aesthetic into my wardrobe?

To incorporate preppy pieces into your wardrobe, you can start by investing in classic pieces such as polo shirts, button-down shirts, chinos, blazers, and boat shoes.

Opt for clean and tailored silhouettes and choose colors and patterns that are characteristic of the style. Additionally, accessorize with items like headbands, pearl necklaces, and classic watches to complete the look.

A Polished Appeal

Office Work Preppy Style
A blazer and sweater look is ideal for an office setting. Photo:

The preppy aesthetic is a fashion phenomenon that has stood the test of time. From its origins in the Ivy League to its influence on street style, preppy fashion continues to inspire and captivate. With its classic pieces, timeless elegance, and adaptability, this aesthetic remains a staple in many wardrobes. 

So, whether you’re channeling the sophistication of Ralph Lauren or embracing the individuality of modern prep fashion from brands like Thom Browne, there’s a look for everyone. Embrace the style, make it your own, and let the world see your fashion statement.

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