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

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


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.

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.


Leather Rucksack ($248)

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

Men’s Dual Time Metal Watch ($78)

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

Follow The Lines Round Sunglasses ($14)

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

Come To Bed Red Nail Lacquer ($15)

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


Threadbare Ring ($44)

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


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.

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. 


Quantum Jacket ($135)

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


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.  

Leather Belt ($13)

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


Limited Edition Elastic Sneakers ($58)

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

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.

Elastic Hair Tie Pack ($12.50)

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