The Coolest Preppy Pieces to Embrace This Fall

This fall, take your uniform from the classroom to the catwalk and beyond with a few preppy pieces. From pleated plaid skirts to sleek loafers and striped neck ties, the combinations for modernizing the collegiate look are endless. Ahead, we rounded up everything you need to ace the seasonal style — whether you’re too cool for school or like to play it safe.

Polo Ralph Lauren Soft Pinstripe Suit Jacket

Class is in session! A tailored-to-the-nines blazer — in a positively scholarly pinstripe — looks smart in every respect. Check the nipped-in waist which lends a feminine look to a normally boxy fit.

Remain Birger Christensen Layered Suiting Shirtdress

Count on Remain Birger Christensen to distort the prep trend just enough to get us talking. This oversized button-down-and-mini-skirt one-piece has cool girl energy in spades (plus, it’s a near-replica for one of Prada’s most covetable looks this season at a way lower price point.)

Dior Miss Caro Mini Bag

If you ever wanted your Gossip Girl moment as a full-fledged adult, this quilted Caro Macrocannage by Dior is it. Worn with your best impression of a Constance Billard uniform (and a headband, natch), it’s a handbag that would make Blair Waldorf proud.

Celine Skate Pants

A dupe for the slacks seen in Dead Poets Society, these Celine trousers are an easy wear on school (slash work) time and beyond. Pairing it with a button-up is the obvious choice, but a perfect white tee works just as well.

J. Crew English Silk Tie

High school uniform essential turned runway staple? Take a cue from the many collection (Dior, Valentino and Alexander McQueen included) that prominently featured neckties. Couple it with an overall relaxed silhouette for a school’s-out approach to styling.

Sophie Bille Brahe Petite Peggy Necklace

These aren’t your grandmother’s pearls: the Copenhagen-based designer’s gradient take on a jewellery box classic brings an unexpected element that’s wholly modern (and mega-wearable.)

Thom Browne Pleated Mini Skirt

Every prep-leaning closet needs a plaid mini skirt; noted checks-enthusiast Thom Browne is where to source it from. The layering of two patterns launches this piece from hallway sweet to sartorial chic.

COS Classic Leather Penny Loafers

Whether it’s the aforementioned pleated trousers or plaid skirt, these chunky loafers ground any good collegiate-inspired outfit. Sport them with scrunched-down socks and an oversized crew neck sweater for low-key impact.

Loewe Turn-up Shirt

You can’t mention prep without a crisp button-down or two. Loewe’s unique option — with a prep school-approved stripe and turned-up cuffs — has limitless style potential in your closet.

This article first appeared in FASHION’s September 2023 issue. Find out more here.