Preppy Style Mastery with 20 Original Fashion Essentials

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The Preppy style is a way of dressing with origins in the early 1900s uniforms of elite Northeastern United States preparatory schools and Ivy League universities.

Drawing inspiration from British and American upper-class leisurewear, the Preppy dressing style exudes scholarly elegance and affluent refinement.

Preppy Style

Nowadays, Preppy has several variations of dressing styles that blend Preppy’s conservative aesthetics with on-trend casual elements, continuing to reflect elegance, refinement, elitism, and an affluent lifestyle.

You must know the signature preppy clothes, footwear, and accessories to achieve the preppy look.

Aesthetic and Social Meaning preppy outfit

These prep essentials have stood the test of time and evolved into symbols of heritage, culture, and class, all of which we will explore in this comprehensive guide.

1. Royal Navy Blazers

Preppy royal navy blazer

Synonymous with British Royal Navy uniforms and a testament to status and traditional elegance, the navy blazer is a crucial garment to style preppy.

Flaunted by celebrities like Kate Middleton, the blazer works best with a pencil preppy skirt to create a contemporary look.

Preppy navy blazers men women

The blazer’s midnight-blue defacto color adds an air of class, making it a year-round essential in any preppy wardrobe.

2. Polo Shirts

Preppy style Ralph Lauren Polo shirts

Initially designed by Lacoste in the 1930s for tennis, the polo shirt transcended its sporty roots to become a pivotal Preppy clothing item.

Ralph Lauren’s Polo label further popularized the style in the 1970s. Since then, the polo shirt has become a status symbol, fashioned by celebrities like Zac Efron and Katherine Heigl.

Preppy Polo Shirts Zac Efron and Katherine Heigl

Available in a wide array of pastels besides the classic colors, the Polo shirt’s appeal lies in its blend of casual comfort with thoughtful, traditional lines.

3. Rugby Shirts

Preppy rugby shirts

The rugby shirt, also known as the rugby jersey, originated in the 1830s when the Rugby School of England declared that athletes must wear a battle uniform.

Traditionally, rugby shirts had buttoned openings at the top, similar to polo shirts, but a stiffer collar, horizontal stripes or “hoops” in alternating colors, and a number on the back.

Preppy Rugby Shirts David Beckham and Kendall Jenner

Nowadays, modern rugby shirts have a tiny collar – or none – to provide less material for a potential tackler to latch onto, modern colors, and thicker fabrics.

4. Oxford Cloth Button Down Shirts (OCBD)

Oxford Cloth Button Down (OCBD) Preppy shirt

Launched as a practical solution for British polo players in the early 19th century, the OCBD is a classic Preppy garment.

The style was brought to the U.S. by Brooks Brothers, adopted by many Ivy League students, and championed by celebrities like Reese Witherspoon and Eddie Redmayne.

Preppy Oxford Cloth Button Down Shirt Eddie Redmayne and Reese Witherspoon

Popular in traditional white and pale blue, these shirts pair well with preppy blazers, chinos, loafers, and reps ties.

5. Chinos

Preppy chinos

With roots in the chino fabric designed for the British and French military, chinos trousers are a popular choice for men’s preppy attire.

Sported by American soldiers returning home after World War II, Khaki chinos became common on U.S. streets.

Preppy Chinos Eddie Redmayne and Gwyneth Paltrow

Modern chinos come in a varied color palette, showcased by celebrities like Eddie Redmayne and Gwyneth Paltrow.

6. Cable Knit Sweaters

Preppy Cable Knit Sweaters

With origins back to the Aran Islands, Ireland, cable knit sweaters were adopted by Northeastern preppies as a stylish garment for cold weather.

Preppy Cable Knit Sweaters Chris Evans and Kate Middleton

Nowadays, cable knit sweaters are donned by fashionistas like Taylor Swift and have become synonymous with an idealized countryside life.

7. Cardigans

preppy style Cardigans

The cardigan became popular in the 17th century and is named after the 7th Earl of Cardigan – a British Lieutenant-General who commanded the Light Brigade during the Crimean War.

Ingrained in the preppy subculture, cardigans are worn over Oxford or polo shirts to confer warmth and stylish versatility.

Preppy Cardigans Grace Kelly and Taylor Swift

From creamy hues to pink shades that signal the arrival of spring – as the cardigans showcased by Preppy icons like Grace Kelly and celebrities like Taylor Swift – cardigans are a must in the preppy wardrobe.

8. Plaid Skirts

Preppy style plaid skirts

Plaid skirts, particularly the ‘schoolgirl’ skirt, are a quintessential preppy clothing item with roots in the Scottish Highland clans.

Worn with knee-high socks, loafers, and crisp Oxford shirts, plaid skirts exude a sense of European heritage and tradition, particularly those in a tartan pattern.

Preppy Plaid Skirt Ashley Roberts and Blair Waldorf

Adorned by fashion-forward celebrities like Ashley Roberts and Blair Waldorf from “Gossip Girl,” plaid skirts inject a pop of classic pattern into this unique aesthetic.

9. Countryside Jackets

Preppy Style Barbour Jackets and Coats

Some of this style’s most popular coats and jackets are from the British brand Barbour.

With a heritage steeped in the countryside and coastal living, Barbour coats are a staple in the preppy circles for practicality and traditional style.

Preppy Barbour Jacket Olivia Palermo and John Wrazej

In earthy tones with tartan linings, Barbour jackets have been popular with royals like Queen Elizabeth II, actors like Steve McQueen and Daniel Craig, and influencers like Olivia Palermo and John Wrazej.

10. Bermuda Shorts

Preppy style bermuda shorts

Named after the British Overseas Territory, Bermuda shorts became popular in the mid-20th century and soon found their way into the preppy style.

Bermuda shorts in pastel shades pair well with polo shirts, button-downs, and boat shoes and are ideal summer wear.

Preppy Bermuda Shorts

Loved by JFK and spotted on Reese Witherspoon, Bermuda shorts offer a relaxed yet sophisticated look, epitomizing the laid-back elegance inherent in preppy style.

11. Boat Shoes

preppy style boat shoes

Designed in the 1930s for better traction on slippery boat decks, boat shoes leaped from their utilitarian origins into the preppy world.

Preppy boat shoes on Blake Lively Chris Pine

Thanks to brands like Sperry Top-Sider and celebrities like Chris Pine and Blake Lively, the boat shoes have become key preppy footwear, reflecting the subculture’s maritime roots.

12. Penny Loafers

Preppy Penny Loafers

The loafer-style shoe has several plausible origins, from Norwegian fishing shoes, Iroquois moccasins, and Regency-era opera pumps called by King George VI as his favorite shoes to ‘loaf’ around in, or most likely, a combination of all.

In the U.S., the loafer shoe became popular with the wealthiest and fanciest social classes as a casual style yet suitable for leisure activities.

Preppy Penny Loafers

Introduced in the 1930s as part of the uniform of American preparatory schools, the shoe was nicknamed the ‘penny loafer’ after students started hiding penny coins in the shoe slot.

Spotted on pop and style icons like Michael Jackson and Alexa Chung, penny loafers are popular in black, brown, and burgundy shades.

13. Brogues

Preppy style brogue shoes

Brogues have roots in a rudimentary shoe originating in Ireland and Scotland.

Used as outdoor or country footwear, given the perforations that allow the upper to dry more quickly in wet climates, Brogues were initially considered inappropriate for casual or business occasions.

Preppy Brogue Shoes Naomi Watts and Ryan Gosling

However, in the early century, American country clubs repurposed brogues into the central business dress shoes and critical footwear of Preppy styles.

14. Oxford Shoes

Preppy style Oxford shoes

Called Balmorals after Balmoral Castle, Oxford shoes first appeared in Scotland and Ireland and were later named Oxfords after Oxford University.

Preppy Oxford Shoes Katie Holmes and Eddie Redmayne

In the late 1800s, the shoe style was introduced in North American colleges as the ‘Bal-type’ – about ‘Blucher-type’ shoes.

15. Pumps

Preppy Pumps

Called Pump shoes in America and Court shoes in the U.K., this shoe style has a low-cut front or a vamp, with either a shoe buckle or a black bow as ostensible fastening.

Preppy Pumps Taylor Swift Manolo Blahnik

By the turn of the 19th century, shoe buckles were replaced by black bows, and Preppies adopted the style as opera slippers for women or formal wear in patent leather for men.

16. Repp Ties

Preppy style repp ties

With roots in British schools, scout clubs, and army regiments, repp ties have distinct stripe and color combinations and are an essential American preppy style accessory.

While Brooks Brothers is credited with introducing them in the U.S. and inverting the direction of the stripe for an American twist, Ivy League students and many celebrities like JFK made these accessories iconic.

17. Headbands

Preppy style Headband

The headband is an accessory with ancient Egyptian origins adopted by the preppy subculture for its practicality and ability to add a pop of color or print to any preppy outfit.

Worn by celebs like Jackie Kennedy and Blair Waldorf of “Gossip Girl,” headbands can be in solid colors or with polka dots, naval, or floral patterns.

18. Knee-High Socks

Preppy knee-high socks

The school-inspired knee-high socks style is an emblem of a youthful and fashionable nod to the charm and innocence of childhood.

Celebrities like Ariana Grande and Alexa Chung wear them with skirts and dresses to add a playful yet traditional touch to their outfits.

19. Monogrammed Bags and Scarves

Preppy style monogrammed bags and scarves

Monogramming dates back to the ancient Greek and Roman empires and marks and showcases distinction.

Monogrammed (or personalized) tote bags and scarves are the most common in this style, used to deliver a unique sense of identity and exclusivity.

Brands like Mark and Graham and celebrities like Reese Witherspoon have championed monogrammed scarves and bags, reinforcing the importance of individuality.

20. Pearl Necklaces

Preppy Style Pearl Jewelry

Used in jewelry for millennia, pearls are associated with wealth and status.

Pearls are classic accessories for women, particularly earrings, bracelets, and necklaces.

Worn by influential figures like Jackie Kennedy and modern celebrities like Sarah Jessica Parker, pearls add a touch of elegance to any preppy outfit.

What to Know Before Creating Your Preppy Look

The preppy style is synonymous with a polished and pristine appearance rather than street-style distressed jeans or ripped tees.

Keeping your clothes immaculate is essential – think freshly laundered shirts, crease-free trousers, and spotless footwear.

preppy clean polished clothes

Fabrics should be high-quality and well-maintained, the color palette should be sharp and clear, and patterns should represent this traditional look.

Ensure your collar is sharp, your cuffs are crisp, and your rep tie is on point for a refined and immaculate presentation at the heart of the timeless Preppy style.

1. Wear it garments

The Preppy dressing style makes a statement through meticulous attention to fit and tailoring.

Well-tailored clothing is one of the cornerstones of this style.

preppy tailored outfits

The goal is to achieve a balance between structured elegance and effortless comfort.

Wear garments shaped to your body without being too tight or too loose.

Whether it’s a crisp button-down shirt, a preppy-style blazer, or a classic A-line skirt, the garment should accentuate your figure gracefully.

Avoid anything that looks baggy, as it can give off a disheveled appearance, and steer clear of overly tight clothing that can come across as too restrictive and counter to the preppy ethos of composed nonchalance.

2. Layering is key

Mastering the art of layering is quintessential to nailing the Preppy style.

This approach adds depth and texture to your ensemble and is practical for transitioning between seasons.

Begin with classic collared shirts as a base, and elegantly layer them with knit cardigans or V-neck sweaters.

Preppy style layering

Topping off with a preppy-style blazer or a tailored jacket can further refine your look.

Don’t shy away from incorporating vests or pullovers for added sophistication.

Be mindful of color coordination and pattern mixing to ensure a harmonious blend.

The Preppy style is also adaptable; you might layer a trench coat over a sweater in cooler months, while a light cardigan over a dress can be perfect in warmer weather.

Successful layering creates a polished, functional, and seasonally appropriate Preppy look that exudes understated elegance and finesse.

Similar Styles to Preppy

Ivy League | Northern Preppy | Southern Preppy | Sloane Ranger | BCBG | Old Money | Dark Academia | Light Academia

Professional Styling Advice

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After years of managing hundreds of fashion brands from London's office of a global retailer, Mandy has ventured into freelancing. Connected with several fashion retailers and media platforms in the US, Australia, and the UK, Mandy uses her expertise to consult for emerging fashion brands create top-notch content as an editorial strategist for several online publications.

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