Preppy Style Is Making a Comeback—12 Outfits That Define the Aesthetic

When I hear "preppy style" usually what comes to mind is a flood of prep-school uniforms, stuffy plaid, and basically the entire wardrobe of Gossip Girl. While those things are definitely iconic elements of preppy style, they tend to feel a bit dated since the prevailing aesthetic in fashion lately has gone in a different direction. That is, until now. 

I never thought I'd be saying this, but preppy style is making a huge comeback this year. The difference, though, is that instead of sharp tailoring and muted colors of yore, the fashion world is taking its inspiration from Princess Diana's '80s looks and incorporating sporty elements, pastel colors, and relaxed silhouettes. The goal look is a mix of retro Lady Di and what Chriselle Lim is dubbing the "rich mom" aesthetic. Think pearls, sweater vests, and headbands, all with a distinctly new spin that feels fresh and new.

I'll just let the below 12 preppy outfits do all the explaining so if you're still with me then scroll down to see how fashion girls are taking this look and running with it and then shop the specific micro-trends they're wearing.


(Image credit: @chrystelleeriksberger)

The Micro-Trend: The Sweater Drape

How to wear it: Take a chunky knit sweater and knot it over your shoulders atop a basic tee or tank for a prep-school kid vibe.


(Image credit: @annawinck)

The Micro-Trend: Exposed Collars

How to wear it: Layer a sporty crewneck over a crisp collared shirt, pulling the collar and cuffs out from under. For an extra preppy feel, style with socks and loafers.


(Image credit: @itsmekellieb)

The Micro-Trend: Pleated Skirts

How to wear it: Pleated mini skirts or a mini dress like Kellie's looks all the cooler with prim and proper accessories like a lady bag and headband.


(Image credit: @matildadjerf)

The Micro-Trend: Sweater Vests

How to wear it: Similar to the crewneck layering idea above, knit vests are best worn oversized atop a button-down shirt with just the collar peeking out.


(Image credit: @cassandra.cadwell)

The Micro-Trend: Tennis Player-Chic

How to wear it: Suddenly, the fashion world is infatuated with the pleated skirts, retro sneakers, and general aesthetic of playing tennis—no actual skills required. Get the look by combining one or all of these tennis player trends into a single outfit. 


(Image credit: @aude_julie)

The Micro-Trend: Cable Knit

How to wear it: Cable knit on its own veers into "grandpa" territory pretty quickly, so to make it feel modern, wear it with a current denim trend like slouchy jeans.


(Image credit: @sofiamcoelho)

The Micro-Trend: Logo Embroidery

How to wear it: Designer brand or not, embroidered logos have always seemed preppy for some reason, especially when they're stitched onto polo shirts. For a modern spin, try it on a cropped top.


(Image credit: @chloepierreldn)

The Micro-Trend: Tall Socks with Sneakers

How to wear it: Retro sneakers and tall socks, AKA the '80s Princess Diana look, couldn't be any more iconic. Lean into the sportiness by wearing with a tennis skirt.


(Image credit: @lauranadineherbert)

The Micro-Trend: Polo Tops

How to wear it: Try a simple sweater with a polo-style neckline to embrace a more subtle version of preppy style.


(Image credit: @nlmarilyn)

The Micro-Trend: '80s Suiting

How to wear it: Yet again, we have Princess Diana to thank for popularizing this look. She was a big fan of the pastel suit and though hers were skirt suits, a 2020 version would look like this with a big blazer, trousers, and a stretchy headband.


(Image credit: @maria_bernad)

The Micro-Trend: Tailored Bermuda Shorts

How to wear it: Tailored shorts on their own are pretty versatile but worn with a sweater vest and boxy tee, it's a look that reads preppy "dad".


(Image credit: @emilisindlev)

The Micro-Trend: Oxford Shirting

How to wear it: Striped oxford shirts—what could be preppier than that? Mix yours with athletic shorts and sporty sandals for a more dressed-down and fashion girl-approved approach.

Up next: the 5 "ugly" trends descending on the fashion world this fall.

Senior Editor

Anna is an editor on the fashion team at Who What Wear and has been at the company for over five years, having begun her career in the Los Angeles office before relocating to New York, where she's currently based. Having always been passionate about pursuing a career in fashion, she built up her experience interning at the likes of Michael Kors, A.L.C., and College Fashionista before joining the team as a post-graduate assistant editor. Anna has penned a number of interviews with Who What Wear's cover stars over the years, including A-listers Megan Fox, Issa Rae, and Emma Chamberlain. She's earned a reputation for scouting new and emerging brands from across the globe and championing them to our audience of millions. While fashion is her main wheelhouse, Anna led the launch of WWW Travels last year, a new lifestyle vertical that highlights all things travel through a fashion-person lens. She is passionate about shopping vintage, whether it be at a favorite local outpost or an on-the-road discovery, and has amassed a wardrobe full of unique finds. When she's not writing, you can find her shooting street imagery on her film camera, attempting to learn a fourth or fifth language, or planning her next trip across the globe.