The Most Timeless Fall Aesthetic Is Here—8 Staples You'll Need to Get the Look

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(Image credit: @cocobassey)

Every fall, I'm quick to put away the bright strobes of color that have graced my wardrobe all summer long in favor of an aesthetic that truly never goes out of style—the preppy look. Gossip Girl may have finished airing a year ago, but for me, the show plays over and over again every fall in my closet. We've entered an era of elevated prep that takes us steps away from the comfort-first vibe that it once had and toward boxy blazers, elevated wardrobe staples, and plenty of miniskirts. We've reached a point where you can easily throw in a pair of long socks to up the façade that you're just a teenager getting ready to take over the halls of your elite private high school.

If you're not sure where to begin when it comes to this aesthetic, I've done the groundwork for you. Below, find the eight staples that you'll need to get the 2023 iteration of preppy style.

1. Thick Headband

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(Image credit: @emmanuellek_)

Thick activewear headbands have made their move on the fashion set, and nothing excites me more than the fact that they're so cost effective. If you have an outfit formula that you wear on repeat and want to make it feel fresh, just add a headband.

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2. Minimal Loafers

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(Image credit: @anoukyve)

Loafers will always be part of the preppy uniform, but now more than ever, they're truly a staple. Take a step away from the chunky styles and choose minimal styles to make your look feel even more fashion-forward. I've been loving loafers that come in mule shape and form.

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3. Oversize Shirting

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(Image credit: @cocobassey)

A good button-down shirt can do wonders for your wardrobe. Throw it over a pair of jeans and you'll be out the door in seconds. I've really worn in my favorite shirts, so I'm currently shopping for more.

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4. Fitted Cardigan

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(Image credit: @annelauremais)

If you like J.Crew-inspired prep, then you surely remember the fitted cardigan. Well, it's back and better than ever. I feel like this is the ultimate French-girl staple.

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5. Tailored Vest

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(Image credit: @fakerstrom)

I can't go into the Who What Wear office without seeing multiple co-workers wearing tailored vests. It's an easy way to seem put-together without sacrificing comfort. Style yours with matching wide-leg pants or a good skirt.

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6. Buttoned Dress

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(Image credit: @_sierramayhew)

I've been starting to see dresses that spotlight gold buttons pop off. If you want your little black dress to seem next-level, just add these buttons and let the rest fall into place.

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7. Preppy Skirt

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(Image credit: @aidabadji_)

I've always been a skirt girl. It's just in my nature. Fall is the perfect opportunity to wear as many skirts as possible and style them well. My favorite way to wear a skirt is with a sweater.

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8. Structured Blazer

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(Image credit: @annabelrosendahl)

I can't end an article about preppy style without mentioning blazers. They'll truly never go out of style and will always be a must for a preppy girl. *Adds to cart*

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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 Bazaar.com, 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, trying the latest fitness craze in New York City, or exploring luxury vintage boutiques.