15 Preppy Outfits That'll Make You Feel Like "Gossip Girl" IRL
Hey, Upper East Siders... đź’‹
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Surprise! Preppy outfits have been sneakily trending upward for awhile now, and we can confidently say that preppy style is back — and in a few different iterations, no less. For example, the Coastal Grandma aesthetic that took over TikTok last summer (think courtside tennis style, breezy shirt-dresses, and New England seersucker) is a fresh version of preppy, as are the Light Acadamia and Dark Academia aesthetics that show love to tweed blazers, heeled loafers, and cozy knits. And yes, the Y2K plaid shorts and varsity jackets that Bella Hadid often wears can totally be considered preppy, too.
Of course, we can’t talk about preppy style without mentioning the prep school outfits that inspire the whole look — an aesthetic that the students of Constance Billard-St. Jude’s know like the back of their hands. The Gossip Girl school uniform has stood the test of time, from Serena van der Woodsen’s pleated school skirt and Blair Waldorf’s statement headbands to Audrey Hope’s cardigans and Julien Calloway’s silk scarves. The common denominator between all four fashion queens is that their outfits are collegiate and crisp — perfect to wear to an ~exclusive~ private school on the Upper East Side of Manhattan or out with your friends.
Nailing preppy outfits and style is all about wearing classic pieces, sometimes channeling that “Old Money” look that TikTok loves so much and other times adding a hint of vintage collegiate sporty influence. You don't have to go, full schoolgirl — preppy pieces can be incorporated into super comfy outfits with a street-style twist. Varsity jackets, plaid mini skirts, neckties, sweater vests, and navy stripes are just a few of the many options you’ll have at your disposal while exploring the preppy aesthetic. Ahead, get all of the preppy outfits and inspiration you’ll need to channel your inner Constance Billard student in 2023.
Cher Horowitz-Inspired Plaid
Do Cher proud in a yellow mini straight out of the movie Clueless. Style it up with a graphic knit to bring this '90s favorite into 2022.
What you'll need: MakeMeChic Plaid Skirt, $27, amazon.com
Vintage-y Cable Knit
The combo of a red cable knit sweater and jeans is an easy preppy outfit to pull off. Grunge down the look with Docs and a trendy shoulder bag.
What you'll need: Fluffy Cable Crew Sweater, $48, abercrombie.com
Cool in Crimson
Layer a crisp white button-down under a logo t-shirt and add a pop of color with cherry red accessories. Preppy fashion never looked so cool.
What you'll need: Asset Cognac Leather Boots, $120, stevemadden.com
Trouser Shorts
When temps get too high for full-on wool trousers, take notes from Barbie Ferreira, who styled long plaid shorts with a super relaxed button-down and choker for an updated prep look.
What you'll need: Vintage Slouchy Plaid Short, $45, urbanoutfitters.com
Sweater (Vest) Weather
Layering a sweater vest over a preppy button-down is perfect for days when you want to get away with wearing leggings while still looking like ~fashion.~
What you'll need: Knitted V Neck Sweater Vest, $29.99, amazon.com
Preppy Prints Turned Cozy
Trousers aren't just for internships and interviews — they'll pair perfectly with your fluffiest, coziest cardigan, balancing out the look for a laid-back, preppy vibe.
What you'll need: Plaid Straight Leg Pants, $40, forever21.com
Plaid on Plaid
Don't be afraid to wear a monochrome look with prints. Hailey Bieber knows that plaid is practically a neutral when it's in classic shades like grey, black, or white.
What you'll need: Plaid Straight Neck Mini Dress, $28, ardene.com
Belts, Caps, and Bags
The accessories can make or break your preppy outfit. Classic bags, leather belts (for pants or dresses, ofc) and cabby hats will take any ensemble to the next level.
What you'll need: Faux Wool Cabby Hat, $16.90, windsorstore.com
Gothic Peacoat
This outfit is proof that preppy style can take on any vibe – even Victorian goth. Pair up preppy items, like a peacoat that you'll wear for years, with edgy details, like these leather over-the-knee boots.
What you'll need: Fulton Wool Coat, $345, marcellanyc.com
Varsity Jacket
Sift through your local thrift store (or raid your dad's closet) for a retro letterman jacket that gives off allll the preppy feels. Pair with a vintage-y concert tee and pants.
What you'll need: Varsity Baseball Lettermen Jacket, $39, Amazon.com
Nautical Cardigan
This is the ultimate preppy outfit. An oversized stripe-trim cardigan adds effortless elegance to a white tee and jeans. Keep accessories low-key so the sweater steals the show.
What you'll need: Marisole Cardigan Dress, $191, saylor.nyc
Clean White Turtleneck
A fitted white turtleneck is a tried and true preppy favorite. You can layer under your favorite sweater, tuck it into high waisted jeans, or double down on preppy vibes with a nautical striped skirt.
What you'll need: Pima Micro-Rib Turtleneck, $50, everlane.com
Updated Penny Loafers
Make your classic penny loafers feel fashion-y with cropped jeans and cute striped socks — any outfit instantly becomes preppy when you add a pair of black slip-on loafers.
What you'll need: Rate Moc Toe Loafers, $65, drschollsshoes.com
A Classic Varsity Sweater
Nothing says "preppy" like a classic Lacoste varsity knit. Try wearing yours oversized with slim joggers or dress it up with a slim trouser and boots.
What you'll need: V-Neck Cable Knit Wool Sweater, $132, lacoste.com
Hannah is the Assistant Fashion & eCommerce Editor at Seventeen, covering style, shopping, trends, and money.
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