Back-To-School Style Inspiration: Post-Grad Plaid & More!

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.

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  • Read on for ideas on how to channel prep school without looking like you’re actually headed to chemistry class.

  • Schoolgirl

    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.

  • Zara

    Poplin Shirt ($70)

    This streamlined, classic shirt is a must for any 9-to-5 wardrobe.

  • Lands' End

    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.  

  • Sophia Webster

    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.

  • Madewell

    Leather Rucksack ($248)

    Backpacks may be a classroom staple, but this posh leather version is suitable for those already wielding a high school diploma.

  • Casio

    Men’s Dual Time Metal Watch ($78)

    This chunky gold watch is the perfect finishing touch to any preppy ensemble.

  • UO

    Follow The Lines Round Sunglasses ($14)

    Stylishly shield the sun with these John Lennon-inspired shades.

  • Butter

    Come To Bed Red Nail Lacquer ($15)

    Give your outfit a classic touch with this timeless red nail polish.

  • Catbird

    Threadbare Ring ($44)

    These ultra-dainty rings play up the feminine vibe of the schoolgirl look.

  • Schoolboy

    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.

  • Mango

    Pinstripe Wool-Blend Suit Trousers ($70)

    These pinstripe pants can be made office-appropriate with heels or weekend-ready with sneakers a la our street style inspiration. 

  • Community

    Quantum Jacket ($135)

    Toss on this military-inspired topper to add a dose of borrowed-from-the-boys chic to any ensemble.

  • Equipment

    Sleeveless Signature Bright White Cotton ($168)

    A sleeveless button-up keeps you simultaneously cool and polished.

  • 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.  

  • H&M

    Leather Belt ($13)

    Follow in Karolina’s footsteps and team pinstripe pants with a basic leather belt like this one from H&M.

  • Bensimon

    Limited Edition Elastic Sneakers ($58)

    These slip-ons are as comfy as they are stylish—a winning combination if you ask us.

  • Coach

    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.

  • J.Crew

    Elastic Hair Tie Pack ($12.50)

    Use these hair ties to forgo girly pigtails in favor of a messy side braid.

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