The modern Preppy style is the ideal way to dress wealthy but with a trendy twist.
The traditional Preppy fashion aesthetics, like polos, chinos, navy jackets, oxford shirts, and loafers, remain staples but with a twist.
The modern Preppy style includes clothes, footwear, and accessories from the latest trends to create a contemporary look.
In this article, we’ll cover 10 modern preppy-style outfit ideas curated by our expert stylists to help you dress like a chic collegiate.
1. School Uniform
The blazer remains the most recognizable clothing element of a classic Preppy aesthetic outfit.
Made of wool or cotton, with a structured cut, notch lapels, and two or three buttons on the front, this versatile clothing piece elevates and oozes sophistication.
Take note of KENZO’s blazer as part of their Spring/Summer collection for a contemporary approach to a modern Preppy style.
The blazer must have a lightweight wool blend and a relaxed yet tailored silhouette, suitable for casual and formal occasions.
Choose vibrant plaid patterns like dark blue, red, and green and contrasting white buttons on the front and sleeves for a subtle touch of elegance.
2. Oxford College
Traditional preppy cropped vests were made of cotton, wool, or tweed and featured classic patterns like stripes, plaids, or houndstooth.
Often spotted wearing tweed blazers, jackets, and pants in classic patterns, Princess Diana was a big fan of the V-neck vest over shirts.
Wear cropped vests with necklines – like the one below, showcased at Paris Fashion Week SS23 – over oversized shirts for a touch of modernity to a classic Preppy look.
3. Plaid on Plaid
Worn in the past as a school uniform, plaid skirt suits are one of the most classic preppy ensembles you can wear.
The look consists of a plaid pattern blazer and skirt – in traditional tartan, houndstooth, or windowpane – in matching accessories and coordinating colors.
The Preppy plaid skirt suit hasn’t changed much; the mini skirt got shorter, and the blazer boxier, almost oversized.
Pair the skirt suit with sleek ankle boots or heeled sandals with knee-high socks, a cable knit sweater, and a leather handbag.
4. Tennis Ready
Stylish and comfortable, tennis dresses are ideal for creating an athletic Preppy look.
Classic preppy-style tennis dresses have an American style of short-sleeve design and skirt – a la Tommy Hilfiger.
In comparison, MARINE SERRE’s SS23 sleeveless tennis dress is the perfect example of a modern Preppy style.
The dress is made from a blend of stretchy black fabric with body contour cuts on the sides, giving the dress a modern, edgy twist.
If you go for a black tennis dress, pair it with white sneakers in a contrasting color (white), a white headband for a sporty look, or a black collar for a touch of controversial Alt vibe.
5. Boho Clash
True to its English-Scottish origins, the Preppy style employs a lot of traditional patterns from the island’s clans and highlanders.
Instantly recognizable thanks to its distinctive diamond motif, the Argyle pattern is heavily featured on anything Preppy, from vests to sweaters, skirts, socks, hats, and scarves.
The Argyle pattern blends many Bohemian elements to create edgy boho-style looks.
6. Grunge Vibes
While the classic Preppy style jackets feature plaid patterns, structured shoulders, and a body-fitted cut, COACH’s reimagined Clueless jacket, showcased during their SS23 collection, brings a unique vintage Preppy vibe.
The jacket has a distressed and relaxed Grunge style in a slightly oversized fit.
The Preppy Grunge look works wonders paired with another 80s fashion statement, such as Jelly shoes or Converse.
7. Fresh Ivy League
Emerged in the 40s and sported by Ivy League students from Harvard, Yale, and Princeton – as their way to differentiate from mainstream culture – the original Preppy style was built around English attire.
The style was crisp, classic, and elegant, comprised of well-tailored jackets, polo shirts, conservative-cut trousers, blazers, loafers, and neckties.
The Ivy League style reached new heights in the 50s and 60s, as college athletes started to wear Preppy clothes while playing tennis, golf, or sailing, and reached peak popularity in the 80s thanks to “The Preppy Handbook” movie.
Nowadays, the modern Ivy Preppy Look incorporates the same stylistic elements but in a lesser fit, even loose and oversized.
The modern American Cool Preppy Look features a multi-colored college sweater in Tommy Hilfiger style paired with a formal shirt, tie, and baseball cap.
This trendy outfit balances casual and formal styles, making it suitable for various occasions.
The sweater adds a sense of academic achievement, while the baseball cap adds a casual touch.
Mixing high and low-end pieces makes this look accessible and versatile.
9. Streetwear Prep
Featuring oversized blazers over oversized shirts, the Streetwear Preppy Look combines the sophistication of Preppy style with the comfort and edginess of streetwear.
Adding sophistication to the outfit while providing a comfortable and relaxed fit, the oversized blazer is the focal point of this look.
The oversized shirt is another crucial element of the Streetwear Preppy Look, as it adds the streetwear edge to the overall outfit, creating a sense of effortless cool.
Accessorize with chunky sneakers, backpacks, or hats to complete the streetwear-inspired vibe.
10. Baddie Prep
Another way to create a modern Preppy style is with a body-fitted sweater over a collared shirt with oversized sleeves, as presented by MIU MIU in her SS23 collection.
Start with a classic white button-up shirt with oversized sleeves. Tuck the shirt into a high-waisted, plaid skirt or tailored pants.
Choose a body-fitted sweater in a solid color that matches the bottoms; the V-neck sweater should fit snugly but without being too tight or uncomfortable.
Layer the sweater over the shirt, letting the sleeves and the collar peek out from underneath to add a touch of Baddie style.
About Preppy Fashion Style
The Preppy style is a type of collegiate clothing style worn by Ivy League students in the 50s and 60s to differentiate from mainstream culture.
The Preppy style has a conservative, clean-cut look, with well-fitted and ironed polo shirts, chinos, and blazers with stripes, plaid, and argyle patterns.
What Does Modern Preppy Style Mean?
The original Preppy style in the 40s, 50s, and 60s emphasized neatness and attention to detail, with clothes well-fitted and ironed.
In contrast, the contemporary Preppy style has evolved to incorporate unique stylistic elements and bright colors, such as floral print polo shirts with skinny chinos and oversized, distressed jackets.
What is the Preppy High School Style?
Preppy in high school is a fashion look comprised of the school uniform mixed with timeless Preppy elements such as blazers, polo shirts, sweaters, turtlenecks, chinos, button-down shirts, cardigan sweaters, loafers, headbands, and ties.
Is Preppy Still in Style?
While the traditional Preppy style has evolved to adopt new garments, footwear, accessories, and aesthetics from other styles, Preppy fashion is still a style of its own and in huge demand.
Contemporary designers and brands incorporate Preppy elements into their collections, making polo shirts, chinos, and boat shoes popular among young fashionistas.
Creating a modern Preppy style is possible with the correct wardrobe staples.
Blazers, cropped vests, chinos, plaid skirt shirts, tennis dresses, cricket sweaters, polo shirts, Clueless jackets, rugby shirts, turtlenecks, cardigans, and neckties are critical bases for any contemporary Preppy look.
To create a modern Preppy style, you must blend contemporary trends with the style’s classic and timeless clothing pieces.
By taking inspiration from these 10 runway Preppy looks, you can add a fresh, modern twist to your Preppy wardrobe.
Whether you prefer streetwear colors, baddie patterns, or grunge influences, there are endless ways to modernize your Preppy fashion game.
Time to embrace the best of both worlds by combining classic and contemporary outfits to create your own unique modern Preppy style and turn heads with your chic fashion choices.
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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.