8 Fashion Essentials To Complete A Preppy Aesthetic Wardrobe

If there is anything this new decade has taught us is that fashion’s biggest trends of the past are back again. Over the years, we’ve already seen the resurgence of late-‘90s styles, groovy ‘70s aesthetics, and all the early-aughts trends you could imagine. Now, the latest fad to come out of the fashion history books is the preppy aesthetic.

The foundation of this timeless look stems from the early days of the American collegiate lifestyle, specifically the Ivy League. Its crisp and put-together aesthetic includes such polished pieces as a collared shirt and khakis, along with classic sporty gear, like a tennis skirt and polo shirt. Today, owe the preppy style’s mainstream appeal to America’s top heritage brands, including Brooks Brothers, Ralph Lauren, J.Crew, and Tommy Hilfiger, amongst many others.

Today, the preppy style has made quite a comeback and is one of this fall’s biggest trends. Thanks to TikTok trends like “old money” and dark (and light) academia, as well as the well-received (and very stylish) reboot of Gossip Girl, the school-friendly aesthetic is here to stay, and likely will last for a few more seasons to come.

If you’re here for the timeless preppy aesthetic, we’ve gathered all of the outfit essentials, from varsity sweaters to Mary Janes with high-knee socks, to fully complete your wardrobe. Below, find all the preppy fashion items you’ll need now.

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Preppy Aesthetic Outfit Essential No. 1: Pleated Skirts

The pleated skirt, typically in plaid or muted gray color, is an absolute preppy must-have. The classic private school uniform would not be complete without it. With colder weather on its way, it’s also the perfect excuse to pull out your favorite monogram tights or cozy knee-high socks. Not into pleats? Try a simple khaki version instead.

Preppy Aesthetic Outfit Essential No. 2: Button-Downs

A nice, crisp button-down will go very far in your wardrobe. Depending on your preference on fit — anywhere between slim and oversized — a good button-down will become one of your more versatile pieces.

Preppy Aesthetic Outfit Essential No. 3: Mary Janes

If you went to any kind of grade school where a uniform was required you’ve most likely worn Mary Janes at least once in your life. The standard school-girl shoe that features a rounded toe with a simple black strap across the foot and a slight heel has now been updated in trendy ways.

Preppy Aesthetic Outfit Essential No. 4: Varsity Sweaters & Jackets

A varsity jacket or collegiate sweater is the main sporty piece of any prepster’s outfit. Going for one in a dark-hued burgundy or navy will be the best cozy addition for your fall wardrobe.

Preppy Aesthetic Outfit Essential No. 5: Blazers

You can never go wrong with a great blazer. If you’re a fan of the oversized trend you can really spice up your prep look with a cute necktie or even a school crest detail.

Preppy Aesthetic Outfit Essential No. 6: Khakis & Trousers

If you’re more comfortable in pants than a pleated skirt, a sturdy pair of khakis or trousers are a great preppy staple.

Preppy Aesthetic Outfit Essential No. 7: Loafers

Loafers are huge this year, especially with a chunky silhouette. Edge up your preppy style and add an elevated loafer to your fall shoe rotation.

Preppy Aesthetic Outfit Essential No. 8: Classic Jewelry & Statement Socks

No outfit is truly complete without accessories. For the preppy aesthetic, stock up on plush statement socks (preferably knee-high) and simple yet elegant jewelry, like gold hoops, pearl strands, and a diamond tennis bracelet.