Clothes for a Perfect Style and Look

What is Preppy Style?

The Preppy style is a distinct 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.

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.

These Preppy 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.

Main Preppy Clothing

1. Blazers (Royal Navy Aesthetic)

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 works best with a pencil Preppy skirt to create a contemporary look.

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

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.

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

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.

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)

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.

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

5. Chinos

With roots in the chino cloth fabric designed for the British and French military, chinos are the most popular preppy-style trousers.

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

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

6. 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.

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

7. 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.

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

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.

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

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.

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

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.

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.

1. 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.

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

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

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

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

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

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.

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

4. Oxford Shoes

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

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

5. 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.

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.

Core Preppy Aesthetic Accessories

1. 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 celebrities like JFK made these accessories iconic.

2. 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

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

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

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.

Must-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.

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.

Fit and Silhouette

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.

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.

Master Preppy Layering: from Sweaters to Navy Jackets

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.

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.

Does Preppy Fashion Style Change by Season or Trend?

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.

The most popular 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.

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

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.

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.

Can You Mix Preppy With Other 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.

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.

Core Clothing Brands in Preppy Aesthetic

These are the most representative designers and clothing brands to shop for and create a perfect Prep style.

1. Polo Ralph Lauren
2. Tommy Hilfiger
3. Brookes Brothers
4. Lacoste
5. J.Crew
6. Tory Burch
7. Burberry
8. Lilly Pulitzer
9. Perry Ellis
10. Jack Wills

Access the complete list of Preppy Clothing brands here.