Master The Preppy Style With This Ultimate Guide

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What is Preppy Style?

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.

As the early American institutions were built around the British educational system (attire and activities), the Preppy style comprises traditional British aesthetics, patterns, and visuals.

How to dress preppy guide

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

Where is The Origin of Preppy Fashion Style?

Three (3) main areas are credited with creating the Preppy fashion style and its adoption: Northeastern or New England, Upper-Midwest, and American South.

Each area gave the Preppy Fashion style unique aesthetic elements, colors, materials, patterns, and silhouettes that reflect their geographies, weather, and cultures.

1. Ivy League Preppy Fashion Style

(New England)

Hailing from New England, the Ivy League Preppy fashion style (also known as Classic Preppy) is the earliest Preppy dressing look ever recorded.

The style’s ‘Ivy League’ name references New England’s students (Harvard, Yale, Princeton, Columbia, Cornell, UPenn, Brown, and Dartmouth) and their uniforms in the early to mid-20th century.

New England Ivy League dressing style

The look is associated with old money, maritime culture, and elite academic institutions and is considered the most traditional, refined, and popular Preppy look.

Essential Ivy League Preppy fashion style clothes include navy blazers, chinos, boat shoes, argyle sweaters, tweed jackets, and Oxford button-down shirts.

Given its East Coast origin, the Ivy League Preppy style’s color palette includes navy, burgundy, forest green, and hues of brown.

2. Northern Peppy Fashion Style

(Upper Midwest)

Hailing from the Upper Midwest of the United States – Iowa, Michigan, Minnesota, North Dakota, South Dakota, and Wisconsin – the Northern Preppy fashion style has a distinct look.

The area is renowned for outdoor sports, hunting, and fishing, and thus, the local Preppy fashion style infuses traditional British aesthetics into rugged, outdoorsy clothing.

Upper Midwest Northern dressing style

The Upper-Midwest Preppy fashion style variation incorporates flannel shirts, duck boots, cable-knit sweaters, thick chinos, and heavy jackets, reflecting the region’s sporting culture and colder climate.

Inspired by the region’s Scottish heritage, Tartan and plaid patterns are popular in the Northern Preppy style.

As layering for warmth is an essential aspect of the Northern Preppy fashion style, the look comprises vests, hats, and thick scarves.

3. Southern Preppy Fashion Style

(American South)

Originating in the Southeastern American states of North Carolina, South Carolina, Georgia, and Virginia, the Southern Preppy fashion style is colorful and has an overall summer vibe.

The American South has a vibrant culture with a rich culture of gentility, traditionalism, and a slower-paced lifestyle.

Southern Preppy style dressing

Compared to the other two style variations, the Southern Preppy fashion style is colorful and lively, reflecting the warmer climate and the region’s culture.

Essential Southern Preppy fashion style clothes include pastel-colored Bermuda shorts, light chino trousers, seersucker suits, bow ties, loafers, and many madras and floral prints.

Outdoor activities like horse racing influence the Southern Preppy fashion style, hence the bright colors and playful patterns showcased by representative brands like Vineyard Vines and Southern Tide.

What Are the Main Clothes in Preppy Fashion Style?

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

As such, the Preppy fashion style is built on signature clothes and accessories that have stood the test of time and evolved into symbols of heritage, culture, and class.

This section will showcase the clothes and accessories at the heart of the Preppy style: their origins, cultural significance, popular colors, and patterns.

1. Blazers (Royal Navy Aesthetic)

Preppy royal navy blazer

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

Flaunted by fashion icons like Kate Middleton, the blazer matches pencil skirts, chinos, and distressed jeans to create a contemporary preppy fusion 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 and 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, originates from 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, various 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 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 cloth fabric designed for the British and French military, chinos are the most popular trousers in the preppy subculture.

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 preppy culture, cardigans are worn over Oxford or polo shirts to confer warmth and stylish versatility.

Preppy Cardigans Grace Kelly and Taylor Swift

Cardigans come in a wide range of colors, from creamy neutrals to saturated hues that signal the arrival of spring, as showcased by preppy icons like Grace Kelly and modern celebrities such as Taylor Swift.

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 the preppy aesthetic.

9. Countryside Jackets and Coats

Preppy Style Barbour Jackets and Coats

Some of the most popular coats and jackets found in the Preppy fashion style 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.

What is the Footwear of Preppy Fashion Style?

A quintessential part of achieving a perfect preppy look is the footwear.

The shoes you choose can make or break your Preppy-style outfit, so picking the right pair is vital.

Here’s a rundown of the main preppy footwear options:

1. 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 world of preppy fashion.

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.

2. Penny Loafers

Preppy Penny Loafers

Erroneously credited to Norwegian fishermen, the loafer shoe has its stylistic origins in the Regency-era ‘Opera pumps.’

Also called ‘court shoe,’ the style was popular with the aristocratic British class since the 1700s and represented the pinnacle of formalwear.

The shoe was renamed in the 1920s as King George VI called them his favorite shoes to ‘loaf around’ in.

Preppy Penny Loafers

In the 1930s, the loafer shoe became the ‘penny loafer’ in America after preparatory school students launched a trend of inserting a penny 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.

3. Brogue Shoes

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

4. 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, where it was initially called ‘Bal-type’ in reference to ‘Blucher-type’ shoes.

5. 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.

What are the Main Accessories of Preppy Fashion Style?

While classic Preppy accessories like prep ties, pearls, or golden watches are perfect, avoid over-accessorizing with leather bracelets, oversized earrings, or HipHop style golden chains.

Over-accessorizing will only take away from the sophisticated simplicity look so characteristic of the Preppy style.

1. 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 are credited with introducing them in the U.S. and inverting the direction of the stripe for an American twist, Ivy League students and celebs like JFK made these accessories iconic.

2. Headband

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 fashion icons from Jackie Kennedy to Blair Waldorf of “Gossip Girl,” headbands can be in solid colors or with polka dots, naval, or floral patterns.

3. 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.

4. 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 preppy fashion and are used to create a 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 within the collective preppy aesthetic.

5. Pearl Necklaces

Preppy Style Pearl Jewelry

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

In preppy fashion, 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 Patterns Define the Preppy Fashion Style?

The essence of Preppy fashion stems from its origins in New England, the Upper Midwest, and the Southeastern states.

Each distinctive pattern, color, or fabric embodies the cultural roots and values intrinsic to the Preppy style, such as Irish and Scottish heritage, high education, and a passion for outdoor sports.

These patterns have transcended time and borders to become essential elements of the Preppy aesthetic:

the main preppy patterns

  • Plaid – originating from Scottish tartans and used in British school uniforms.
  • Argyle – another Scottish-heritage diamond-shaped pattern.
  • Gingham – a checkered pattern has roots in British countryside fashions and was adopted by the American Preppies in shirts and dresses.
  • Madras – a colorful checked pattern originating from Madras (now Chennai), India.
  • Paisley – an intricate pattern with origins in Persia.
  • Stripes – navy blue and white in a reflection of the maritime influence.
    Polka dots, nautical motifs, florals.

What Colors Are Used in the Preppy Fashion Style?

While Preppy fashion styles embrace a spectrum of colors, there’s an art to selecting shades that genuinely embody the essence of this style.

The quintessential Preppy fashion style color schemes are rooted in the elegant navy blues of the East Coast’s charm, hunter greens of the Northern part, and Southern’s vibrant Nantucket red, yellow, and orange.

the main preppy colors

  • Navy Blue – is a dominant color in school uniforms, formal wear, and naval attire.
  • Crimson – a deep red associated with some Ivy League institutions, notably Harvard.
  • Khaki – reflects the influence of military attire.
  • Forest Green – associated with outdoor leisure activities like golfing and hunting.
  • Nantucket Red – a salmon pink hue originating from the trousers sold in Nantucket’s Murray’s Toggery shop.
  • Yellow – the ‘always sunny’ color’ symbolizes the vibrancy of the Preppy lifestyle: leisure, positivity, and happiness.
  • Gold – inspired by the brass buttons on traditional navy blazers, gold signifies tradition, luxury, and sophistication.
  • Pastels – light pink, sky blue, and mint green.
  • Black – used in evening wear and formal event tuxedos- reflects tradition’s importance.
  • White – from tennis outfits to Oxford shirts- is a crucial Preppy color.

Eschew overly vibrant neon colors or gaudy prints in favor of a more understated and sophisticated palette.

Pastels like powder blue, soft pink, and mint green can be beautifully incorporated, especially in spring and summer wardrobes.

What Materials and Fabrics Are Used in the Preppy Fashion Style?

The Preppy style epitomizes timeless elegance; a cornerstone of this is the selection of high-quality, natural materials.

The choice of fabric influences not only the appearance but also the feel and durability of your outfit.

Consider indulging in sumptuous wool or cashmere for sweaters and outerwear while opting for crisp cotton and classic Oxford cloth for shirts.

Common Materials Used in Preppy Aesthetic

Tweed and flannel inject a dose of heritage charm, especially in blazers and trousers, whereas Seersucker adds a playful yet refined texture, perfect for summer suiting.

Beyond just the material, it’s essential to focus on craftsmanship and construction, as your Preppy fashion outfits are investments in quality over quantity.

Have a streamlined wardrobe of well-made garments that will stand the test of time rather than many low-quality items.

Choose clothes that age gracefully, hold their shape, and continue to look impeccable even as trends come and go.

This approach elevates your Preppy aesthetic and embodies the ethos of sustainability and conscious consumption.

Who Are the Most Representative Preppy Fashion Designers?

Dressing preppy is not just about the type of clothes you wear, but also where they come from.

Opt for garments and accessories from time-honored preppy labels and designers for an authentic preppy look.

Ralph Lauren, for instance, is a go-to for its iconic polo shirts and classic silhouettes.

Similarly, Lacoste is renowned for its casual yet chic tennis-inspired attire.

Brooks Brothers is another quintessential preppy brand, offering a range of sophisticated and timeless pieces.

Preppy style designers

These brands, among others, have mastered the delicate balance between casual and elegant that defines the preppy style.

Investing in pieces from these recognized labels ensures you achieve the right fit, fabric quality, and classic style integral to preppy dressing.

Additionally, donning attire from these brands speaks to a certain level of fashion literacy, giving you an edge in nailing the preppy look with authenticity and flair.

How Do You Layer Clothes in the Preppy Style?

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.

What is the Right Fit and Silhouette in the Preppy Fashion Style?

Preppy fashion styles make statements through their 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.

What is the Ideal Preppy Look?

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

Keeping your Preppy 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 be representative of the preppy aesthetic.

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.

Can You Mix Preppy With Other Fashion Styles?

While it’s tempting to experiment with various styles, the Preppy style calls for a considered and focused approach.

Though integrating subtle elements from other styles can add a fresh twist to your outfit, avoiding combining dressing styles with no historical or aesthetic connection to Preppy fashion is crucial.

preppy style outfits

For instance, the grunge or punk looks, with their distressed and edgy elements, would clash with the refined and polished nature of the Preppy style.

Aim for a cohesive look that stays true to the classic Preppy elegance, grace, and poise, ensuring that any additional elements enhance rather than detract from the fundamental Preppy aesthetic.

Check out this article about Preppy fashion styles and substyles to experiment with the new look variations.

How Does the Preppy Fashion Style Change by Season?

Here’s how the Preppy fashion style adjusts across the four seasons:

In spring, preppy fashion styles showcase brighter color palettes, including pastels and light, neutral tones that align with the blooming season.

spring preppy style outfit

The most popular Preppy clothes in the spring are light cotton shirts, chinos, madras checks, and seersucker fabrics.

Shoes-wise, boat shoes and loafers are the most popular pairing choices.

Straw boaters, lightweight scarves, and colorful belts are excellent Preppy fashion accessories in the spring.

In the Summer, preppy fashion styles are characterized by light fabrics and even brighter color palettes, reflecting the season’s vibrancy.

summer preppy outfit

Polo shirts, sundresses, skirts, Bermuda shorts, linen shirts, and lightweight dresses have become the most popular Preppy clothes in the Summer.

Boat shoes, loafers without socks, and sandals are also part of a typical summer Preppy outfit, with sunglasses, straw hats, and minimal designer jewelry.

With a shift towards richer and deeper colors inspired by autumn foliage, Fall returns layering to Preppy fashion styles.

autumn preppy outfit

Sweaters, cardigans, wool skirts, corduroy pants, and light jackets also return.

Layering button-down shirts under sweaters, matched with leather loafers, brogues, or ankle boots, becomes a standard view.

The fall’s most popular Preppy fashion accessories are scarves, light leather gloves, and wool or felt hats.

In the Winter, Preppy fashion styles feature warm fabrics and heavy layering techniques to stay warm while looking stylish.

winter preppy outfit

Heavy wool sweaters, tweed blazers, wool trousers, thick dresses, and Barbour jackets are critical for this season.

Layering is crucial in the Winter, so thermal underlayers, sweaters, and long coats are popular.

Footwear-wise, brogues and leather boots are preferred, matched with thick scarves, wool or cashmere hats, and leather gloves.

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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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