Don't Try Wearing the Preppy Trend Without Exploring These 2023 Updates


(Image credit: @emilisindlev)

I live for preppy style. I ended up falling madly in love with fashion even though I wore a school uniform my entire childhood. The funniest part is that while many of my classmates complained about the restraints of knee-length skirts and uniform dressing, I loved the uniformity. I had so much fun bending the rules by layering on knits over my Oxford shirts and testing out different kinds of knee-high socks. We all wore the same outfit every day yet somehow made it different. It was so interesting for me to watch.

A few years later, I entered adulthood, coincidentally around the time that preppy style really took off with its reemergence into the fashion industry. Designers who stuck with this aesthetic like Burberry, Thom Browne, and Marc Jacobs rejoiced, and so did I, as I got to keep some nostalgic notes from my childhood hanging in my closet. 

The school-girl aesthetic has been having its moment for a few years now, so as I prepare my wardrobe for a big entrance into 2023, I’m thinking about the ways that I can keep my preppy style growing and evolving while keeping in mind that the timelessness is what makes this aesthetic so fun to tap into. Come along with me on this journey by shopping my picks below.


(Image credit: @_sierramayhew)

Skipping: Bright-colored coats

Wearing: Leather trench coats

A personal favorite piece in my preppy wardrobe has always been the classic trench coat. Impressively warm despite its lightweight fabric, this will always be a preppy style staple. As I begin to upgrade my wardrobe for 2023, the time has definitely come to elevate my classic trench by choosing leather this time around.


(Image credit: @chrissyford)

Skipping: Oversize blazers

Wearing: Collarless blazers

This futuristic angle on the classic oversize blazer has won me over. My love for blazers has spanned many years, and while I’ll never tire of them, I’m always looking for the next update to that pristine silhouette. Rip off the collar, and you’ll have my attention.



(Image credit: @laurenegg)

Skipping: Knit vests

Wearing: Tailored vests

Knit vests have certainly reemerged as a preppy style staple in the past few years. I’m happy to be keeping my crochet and cashmere vests near and dear while inviting in a tailored vest to have some fun with layering.



(Image credit: @styledevotee)

Skipping: Cropped pants

Wearing: Loose pants

You can’t own prep without trying on a few tailored trousers along the way. Straight-leg cropped pants had their moment for quite some time, but I’m letting loose with baggy trousers at the moment. They really do all the talking making a basic outfit much more than that.



(Image credit: @tylynnnguyen)

Skipping: V-neck sweaters

Wearing: Half-zip sweaters

There are so many layering opportunities that come into play when you have a half-zip sweater on hand. Imagine a striped T-shirt or your favorite turtleneck coming together with this effortless piece. Just another way to keep warm this winter.


(Image credit: @laurencrowe88)

Skipping: Leather miniskirts

Wearing: Tennis skirts

If you have an Instagram account, I’m sure you’ve come across a tennis skirt or two in your feed these days. They have kind of had a viral moment in the past year, and we certainly will be wearing ours into 2023. Beware, this style sells out crazy fast, so I’d add one to your cart ASAP if you want in.



(Image credit: @chasemarieee)

Skipping: Outdated layering 

Wearing: Cardigans on cardigans

Cardigans have always been a preppy staple, but I’ve been taking notes lately on new styling tips for them. I always feel like I have a brand-new wardrobe when I try wearing things in an unexpected way. As seen above, two cardigans are certainly better than one.



(Image credit: @emilisindlev)

Skipping: Average fabric choices

Wearing: Playful corduroy

If you’re tired of wearing boring style staples, unleash your inner child and play around with corduroy. Introducing this fabric to your closet can bring about a youthful presence that will certainly add a little bit of joy to your life.


(Image credit: @kristenmarienichols)

Skipping: Solid sweaters

Wearing: Color-block knits

My current favorite decade is the ’70s, and incorporating a little bit of the disco-fever era in my wardrobe has become hobby. This is certainly an excuse to test out color-blocking. Fun statement knits are always my go-to this time of year, so I’ll definitely be checking out these styles.



(Image credit: @rendagrella)

Skipping: Beanies

Wearing: Baseball caps

These hats went from being an item that was too casual to wear day-to-day (besides at a baseball game) to a fashion-insider must-have. It’s the most affordable and instantly stylish item you can add to your wardrobe right now.


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Associate Editor

Sierra Mayhew was always destined to work in fashion, but she didn't know it at first. Growing up with no choice but to wear a rotation of school uniforms and activewear, her love for fashion really blossomed when she moved away for college and was able to finally define her very own personal style. Shortly thereafter, she interned at Elle magazine and instantly knew that editorial was for her. After graduating from the University of Notre Dame, she worked for ShopBazaar, contributing regularly to, and finally made her way to Who What Wear, where she is an associate editor. When she’s not working, you can catch her always trying to catch a flight, rollerblading through New York City traffic, or exploring the latest luxury vintage boutique.