Though the words “back to school” used to make us cringe because it meant summer was nearly over, nowadays we get a little nostalgic for that fresh-pencils feeling. So to pay homage to the days of lockers and pep rallies, we’ve found two outfits—and lots of lovely shopping suggestions—worthy of the all-important first day ensemble, albeit with a grown-up twist.
Back-To-School Style Inspiration: Post-Grad Plaid & More!
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Read on for ideas on how to channel prep school without looking like you’re actually headed to chemistry class.
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This look is proof that tartan skirts can indeed work beyond school halls. Simply imitate stylist/blogger Pernille Teisbaek and pair the piece with a crisp button-up blouse, chic leather clutch, and white heels. Et voila: A schoolgirl-inspired outfit with a post-grad plaid point of view.
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Poplin Shirt ($70)
This streamlined, classic shirt is a must for any 9-to-5 wardrobe.
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Plaid Pleated Skirt ($45)
Plaid skirts shouldn’t be relegated to prep school uniforms—simply pair this version with heels and a sophisticated blouse for an outfit that’s far from childish.
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Lola Leather Pumps ($320)
Don’t be afraid to wear white well past summer—these elegant pumps are a fantastic way to incorporate the crisp hue into your fall shoe collection.
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Leather Rucksack ($248)
Backpacks may be a classroom staple, but this posh leather version is suitable for those already wielding a high school diploma.
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This chunky gold watch is the perfect finishing touch to any preppy ensemble.
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Stylishly shield the sun with these John Lennon-inspired shades.
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Give your outfit a classic touch with this timeless red nail polish.
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Threadbare Ring ($44)
These ultra-dainty rings play up the feminine vibe of the schoolgirl look.
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For the less Serena van der Woodsen-inclined, Karolina put a unique spin on the menswear approach to today’s trend. We love how her utilitarian jacket feels less buttoned-up than the expected schoolboy blazer, while her slip-on sneakers are a fresher option than penny loafers.
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These pinstripe pants can be made office-appropriate with heels or weekend-ready with sneakers a la our street style inspiration.
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Quantum Jacket ($135)
Toss on this military-inspired topper to add a dose of borrowed-from-the-boys chic to any ensemble.
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A sleeveless button-up keeps you simultaneously cool and polished.
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Band of Outsiders
Textured Dot Tie ($155)
A schoolboy outfit is not complete without a tie. We love the polka dots on this iteration, as they lend a hint of femininity to the mannish piece.
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Leather Belt ($13)
Follow in Karolina’s footsteps and team pinstripe pants with a basic leather belt like this one from H&M.
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These slip-ons are as comfy as they are stylish—a winning combination if you ask us.
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Madison Sadie Flap Satchel ($498) in Spectator Saffiano Leather
With its structured, briefcase-like shape and minimalist hardware, this masculine satchel is in perfect keeping with the schoolboy look.
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Elastic Hair Tie Pack ($12.50)
Use these hair ties to forgo girly pigtails in favor of a messy side braid.