Prep School-Inspired Pieces You’ll Actually Want to Wear

Graduated from your old prep school uniform? Trade it in for a more grown-up version that’s stylish and age-appropriate. With our roundup of sweet pleated skirts, oxford shoes, letterman jackets, and more, you’ll have a stellar style report card in no time.

?Scroll through our 24 back-to-school picks now!

28.5 Embroidered Argyle Skirt ($545)

?If argyle’s for nerds only, sign us up. We love the back-to-school pattern, especially in the form of this stylish skirt.

Ainea Jersey & Neoprene Ruffle Hem Dress ($341)

?This colour-blocked, minidress features a kicky hem for an ultra-flirtatious touch.

Reiss Luigi Fine Spot Contrast Socks ($25)

?If you want to thoroughly nail the schoolgirl look, a pair of socks, which pair well with oxford shoes, are a must-have.


the styleograph

Carven Double Breasted Crepe Blazer ($840)

?This cropped, double-breasted blazer is the ultimate ladylike cover-up.

Gaelle Bonheur Heavy Cotton Jersey Jacket ($280)

?Who needs a varsity athlete to keep you warm when you can have this cool letterman jacket instead?

Gigi Burris Millinery Barbed Band ($150)

?This barbed headband puts an avant-garde twist on the generally sweet schoolgirl accessory.

No Name 40MM Plato Canvas Wedged Sneakers ($115)

?Dress down a skirt or dress with these canvas wedge sneakers. (Just try not to twist your ankle during gym class.)

Reiss Relaxed Tuxedo Blazer ($370)

?We love the relaxed shape of this classic tuxedo blazer!

Opening Ceremony Loafers ($370)

?Looking for a more playful pair of shoes? Try these fun checked oxfords.


Vanessa Jackman

Reiss Bea Bow Embellished Shirt ($195)

?This darling bow top is so Blair Waldorf, don’t you agree?

Reiss Almira Metal Bar Skinny Belt ($95)

?Use this sleek, skinny belt to belt your fall and winter coats!

Rodale's Braddock Backpack ($88)

?When you’ve got a lot to carry, this backpack is a casual and convenient alternative to a shoulder bag.

Ted Baker Gumley Leather Skirt ($395)

?We can totally see Sally Draper rocking this leather mini, which comes in a deep oxblood hue that’s perfect for fall.

Ted Baker Helane Embellished Collar Sweater ($225)

?This sweater’s embellished collar and electrifying red colour will make hitting the books or heading to work a tad more exciting.

Reiss Blanche Scallop-Edge Ankle Boots ($340)

?Scallop trim lends a feminine element to these sleek ankle boots.

Ted Baker Osster Pearl Embellished Top ($195)

?Pull a Peter Pan in Ted Baker’s cute collared shirt.


Vanessa Jackman

Vivetta Pleated Neoprene Skirt ($346)

?Dress down this neoprene skirt with a t-shirt and lace-up oxfords.

Vivienne Westwood Plaid Cool Wool Capri Pants ($560)

?We’re not 100 per cent sure if these punchy plaid trousers are dress code-proof, but they certainly make a stylish statement.

Rodale's Marl Puzzle Dress ($90)

?This staple piece has a classic, feminine shape that lends itself to multiple styling possibilities. Try it with ankle boots and a statement jacket.


Vanessa Jackman

Versus Safety Pin Viscose Crepe Skirt ($280)

?Edgy safety pin embellishments help balance out this skirt’s sweet flared silhouette.

Saint Laurent Babies Mary Jane Shoes ($832)

?The Mary Jane’s sparkly, grown-up cousin called, and she’s definitely going dancing once class is out!

Olympia Le-Tan Webster’s New World Dictionary Clutch ($2050)

?Did your boss just use a word that went way over your head? We can’t help you there, but at least you can look like a vocab nut with this cheeky clutch.

Rodale's 3/4 Sleeve Wrap Top ($65)

?Channel your inner ballerina in this slightly stretchy, flattering wrap top.

3.1 Phillip Lim Berlin Loafers ($664)

?These glossy loafers will add a cool element to a simple button-down and jeans.

?Ever have to wear a school uniform? Did you love or hate it? Let us know in the comments section below!