Prep School Style

As the air turns crisp and the leaves start to change, fall fashion finds itself at the intersection of tradition and trend. This year, the prep school aesthetic—rooted in heritage, structure, and polished ease—is making a decisive return. Whether you’re sending kids back to school or simply dressing the part, the season’s collections are filled with updated classics that nod to ivy-lined campuses and autumn afternoons spent under changing trees.

From blazers to loafers, these are pieces that tell a story: of confidence, refinement, and a touch of collegiate charm. But this isn’t the head-to-toe uniform you remember—it’s a fresh take that blends timeless structure with modern proportions, luxurious fabrics, and unexpected pairings. Whether it's a madras dress in an unexpected silhouette, a polo dress layered under an oversized mac coat, or a pleated skirt might be worn with a chunky fisherman sweater, the prep look is evolving, but its essence—polished, put-together, and just a little bit nostalgic—remains irresistible.

Knit Polos - A polished yet easy-to-wear alternative to the classic button-down, knit polos strike the perfect balance between sporty and sophisticated. This season’s versions feature feminine crochet details or rugby stripes in soft cotton blends, making them ideal for layering under blazers or wearing solo with wide-leg trousers. The polo is also being transformed into easy going dresses like this and this, perfect for pairing with sneakers on off-duty days.

A Timeless Blazer - Nothing says “prep” quite like a well tailored blazer. Whether you opt for heritage tweed (this brand's tailoring is beyond!), a linen houndstooth, or a double-breasted silhouette with gold buttons, a blazer instantly elevates everything from denim to midi skirts. It's also the perfect stylish and light layer for September temps, but can still be layered under coats when you really need to bundle up. I linked a few classics, but I find brands usually come out with more blazers later on in the season.

Loafers - This schoolyard staple is all grown up, whether you opt for a pair with clean lines, block heels, or subtle embellishments. They’re versatile enough to wear with ankle jeans for weekend errands or with a mini skirt for a more polished look. I've collected quite a few pairs over the years from the iconic horsebit loafer to these super comfy sneaker/loafer hybrids.

Button Up Shirts - The backbone of any preppy wardrobe, a perfectly tailored button-up shirt works in endless ways—tucked into pleated skirts, layered under sweaters, or worn open over a tee for a more relaxed spin. This fall, look for versions in classic white, Oxford blue, or subtle stripes.

Corduroy Trousers - Soft, textured, and quietly luxurious, corduroy trousers are a quintessential prep staple for fall. Opt for straight cuts (I just got these and they're awesome - get 15% off with "Stacie15") in rich hues like camel, chocolate, or deep green, and pair them with loafers or brogues for a look that’s both campus-ready and city-smart.

Cable-Knit Sweaters - A prep classic that never truly leaves the spotlight, the cable-knit sweater feels especially relevant this season. Try it oversized with slim trousers, or layered over a collared shirt for a true collegiate vibe. I have this exact cable-knit sweater in 11 colors. (It's getting embarrassing frankly, but I still have a few more colors I want.) It works year round and will never, ever, go out of style. (Be sure to size up so you can layer over buttonups and under blazers.) I also just ordered this cable knit cashmere sweater, which is only $90 and is a perfect color match to wear with this silk dress.

Henleys - Perhaps a lesser known piece in the prep lexicon, Henleys get their name from Henley-on-Thames where rowers wore the jerseys as part of their uniform. These easy knits have a borrowed-from-the-boys appeal, but are offered in a slim, flattering cut for women. Wear a thermal version with jeans for a subtley sexy girl-next door look, or pair a cotton-silk rib knit version with trousers for the office.

Classic Jewelry - Having a few, really good everyday pieces of jewelry is essential for any woman, and preppy favorites include pearl studs, a gold locket, a tennis bracelet (affordable here, heirloom version here!) and a signet ring. I'd also add that a simple watch with a leather strap is a wadrobe essential, and looks perfect peeking out from the cuff of shirts, sweaters and blazers.

The key to wearing prep school pieces now is balance. Pair heritage items with modern silhouettes—like a blazer over fluid wide-leg trousers—or mix in sporty elements, like sneakers with a polo dress. You’re not recreating a uniform; you’re curating a wardrobe that captures the timeless appeal of prep school dressing while feeling current and individual.

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