10 Unique Looks That Define the Modern Preppy Style in 2023

Weekly Newsletter

Keep up with the latest in fashion, beauty and style!

If you’re a fan of the preppy style but want to confer your look a trendy twist, look no further than these 10 runway-inspired modern preppy looks.

The classic elements of preppy fashion, such as clean lines, conservative cuts, and timeless silhouettes, remain staples.

Yet, contemporary preppy styles include the latest trends, modern clothes, and accessories to create fresher, modernized looks.

From bold prints and bright colors to unexpected accessories and layering techniques, these 10 modern preppy looks will inspire you to elevate your preppy fashion game.

Get ready to turn heads with these stylish, chic, and unique modern preppy outfits in 2023.

Preppy School Uniform

Plaid Blazer on White Shirt and Wide Tie

Preppy style blazers by Kenzo
Modern Preppy style blazers as seen at Kenzo SS23 – The VOU

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.

For a contemporary approach to a modern preppy style, take note of KENZO’s blazer as part of their Spring/Summer 2023 collection.

In 2023, 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.


LAUREN Ralph Lauren Plus Size Plaid Bullion Twill Blazer

Taodou Women's Casual Plaid Blazer in Red

Elie Tahari The Archer Plaid Knit Jacket

Oxford College Preppy Look

Cropped Vest on Oversized White Shirt

Preppy Style Vest at Paris Fashion Week
Modern Preppy style vest at Paris Fashion Week SS23 – The VOU

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 preppy vest over shirts.

In 2023, for a touch of modernity to a classic preppy look, wear cropped vests with necklines – like the one below, showcased at Paris Fashion Week SS23 – over oversized shirts.



Sarah Wool Leopard Vest

Double Plaid

Plaid Skirt-Suit with Knee-High Socks and Heels

Preppy style Plaid Skirt Suit by Dior
Modern Preppy style plaid skirt suit as seen at Dior’s Paris Fashion Week SS23 runway – The VOU

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.

In 2023, 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 preppy knit sweater, and a leather handbag.


Sister Jane tweed jacket and mini skirt set

Rails Cody Plaid Blazer & Prim Plaid Skirt

The Tennis Dress

Cut-out Tennis Dress with Hobo Bag

Preppy style tennis dress by Marine Serre
Preppy style tennis dress as seen at Marine Serre SS23 – The VOU

Stylish and comfortable, tennis dresses are ideal for creating an athletic preppy look.

Classic preppy 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 preppy 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 emo vibe.


Herve Leger Ottoman Heart Cut Out Mini Dress

Outdoor Voices Court Cut-Out Minidress


Preppy Boho Clash

Mixing Classic Preppy and Boho Elements

Boho preppy style
Boho clash with preppy style seen at S.S. DALEY SS23 and RALPH LAUREN SPRING 2023 – The VOU.

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.

But, in 2023, the Argyle pattern is blended with many Bohemian elements to create edgy boho-style looks.


Quinn Argyle Sweater Vest

By Anthropologie Pleated Poplin Shirt Dress

Grunge Preppy Look

Dark Plaid Overcoat with Cap and Messenger Bag

Modern Grunge Preppy look
Modern Grunge Preppy look as seen at COACH SS23 – The VOU

While the classic preppy 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 look in a slightly oversized fit.

The preppy grunge look works wonders paired with another 80s fashion statement, such as Jelly shoes or Converse.


ASOS DESIGN oversized brown check overcoat with wool

SHEIN EZwear Lapel Neck Plaid Pattern Belted Tweed Overcoat

Modern Ivy League Look

V-neck Sweater (or Sweater Dress) Over Polo Shirt

Modern Ivy League Preppy style
Modern Ivy League Preppy style as seen at Ralph Lauren Spring 2023 Collection – The VOU

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 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.


Cable-Knit Cricket Midi Sweater Dress

The Iconic Mesh Polo Shirt

Cool American Preppy Style

Multi-colored College Sweater over Formal Shirt and Tie

Modern Preppy color block style
Color block Preppy style as seen at Tommy Hilfiger New York Fashion Week Spring 2023 – The VOU

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.




Streetwear Preppy

Oversized Blazer over Oversized Shirt

Oversized Preppy style
Oversized Preppy style as seen at Copenhagen Fashion Week SS23 and S.S. DALEY SS23 – The VOU

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.


Stella McCartney Oversized Double-Breasted Jacket

Free People Mari Textured Double-Breasted Blazer

Good American Rhinestone Shirt

Baddie Preppy Look

Body Fitted Sweater Dress over Long Sleeve Shirt

Modern Preppy style sweater as dress
Modern Preppy style fitted sweater as seen at MIU MIU SS23 – The VOU

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.


ASOS DESIGN knitted mini sweater dress in rib in black

Bodycon Zip-Front Mini Dress

Modern Preppy Style FAQs

What Does a Preppy Style Mean?

Preppy is a type of collegiate clothing style worn by Ivy league students in the 50s and 60s as their way 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.

Is Preppy Still in Style in 2023?

While the traditional preppy style has evolved into new stylistic elements in 2023, preppy looks are still very much in fashion in 2023.

Contemporary designers and brands incorporate preppy elements into their collections, making preppy clothing items such as polo shirts, chinos, and boat shoes popular among young fashionistas.

What Does Preppy Style Mean in 2023?

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 Preppy in High School?

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.


In conclusion, creating a modern preppy style in 2023 is accessible 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.

Weekly Newsletter

Keep up with the latest in fashion, beauty and style!

Now it’s your turn…

Which of these Preppy fashion styles will you try next, and why?

Which Preppy look of 2023 do you think we’ve missed and should include in our next article update?

Please leave your comments below; we always appreciate your comments and use them to learn, improve, and update these articles.

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.

Similar Articles


Please enter your comment!
Please enter your name here

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.