As we transition from preppy summer outfits into fall, it’s time to embrace cooler temperatures with layered styles and timeless pieces like plaid skirts, blazers, and cozy knits. Whether you’re channeling Ivy League charm or embracing autumn academia, these 28 preppy fall outfits are your go-to looks for a polished, put-together vibe.
Cozy Layers: Cable Sweater & Khakis Combo
A cable-knit sweater is a fall wardrobe staple. Layer it over a crisp collared shirt and pair it with pleated khakis for that nostalgic 90s collegiate look—perfect for brisk autumn days.
Casual Fall Shacket & Leggings Outfit
Go for a relaxed fall look with a stylish plaid shacket paired with black leggings and warm brown boots. A chunky knit beanie and chic tan quilted handbag add a touch of elegance to this casual autumn ensemble.
Navy Sweater Paired with a Pleated Skirt for a Fresh Fall Look
For a classic preppy look with a twist, pair a navy sweater with a white pleated skirt. The tennis-club vibes are undeniable, but knee-high boots give it an edge that’s perfect for fall weather.
Elevate Your Look: Plaid Vest & Khakis Combo
Channel that old-money aesthetic with a plaid vest and khaki trousers. Paired with a button-down shirt, this outfit exudes a sophisticated, boarding-school vibe perfect for the fall season.
Cozy White Sweater & Plaid Skirt Look
For a cute and comfy fall day outfit, pair a cozy white sweater with a trendy plaid mini skirt. Complete the ensemble with ankle boots to keep the look warm and stylish, perfect for crisp autumn days.
Classic Fall Prep: Cardigan & Plaid Skirt Ensemble
Reignite those prep school vibes with a soft white cardigan and plaid mini skirt. Add a chic headband, and you’re giving major Blair Waldorf energy—classic, stylish, and perfect for autumn.
Understated Elegance: Green Sweater with Khakis
This green sweater and khaki combo nails the dark academia aesthetic. Add a bold accessory like a statement bag to elevate the look, proving that preppy can be both understated and powerful.
Bold City Chic: Matching Blazer & Tailored Shorts for Fall
Yes, shorts in fall! Pair a black blazer and white shirt with sheer leggings, chunky loafers, and tailored shorts for that effortless city-chic look as the weather transitions.
Sophisticated Plaid Coat & Turtleneck Outfit
Stay chic in autumn with an oversized plaid coat layered over a white turtleneck and high-waisted black shorts. Add sheer tights, a stylish black handbag, and round sunglasses for a sophisticated, modern edge.
Heritage Style: Blue Shirt Paired with Plaid Pants
Plaid and button-downs are synonymous with preppy fashion. Tuck in a blue shirt and pair it with plaid pants for a heritage-inspired look that’s both casual and refined.
Layered Perfection: Sweater Vest & Black Trousers
The sweater vest trend is here to stay, and nothing says preppy fall like layering one over a white collared shirt. Black trousers ground the outfit, making it an ideal option for achieving a modern academic look.
Polished in Plaid: Tweed Blazer & Mini Skirt Combo
Tweed is a preppy wardrobe essential. Combine a tweed blazer with a mini skirt and loafers for a polished outfit that feels straight out of a Ralph Lauren ad.
Autumn Stroll in Rust Coat & Polka Dot Dress
Embrace fall with a long rust-colored coat over a flowing polka dot dress, creating a charming seasonal look. Pair with suede ankle boots and accessorize with a wide-brim hat and neutral handbag for a stroll-ready outfit.
Ivy League Classic: Beige Cardigan & Plaid Pants
Create instant Ivy League vibes with a beige cardigan and plaid trousers. Pair them with loafers for a cozy-yet-sophisticated fall outfit that’s perfect for casual days.
Timeless Autumn Style: Navy Blazer & Mini Skirt
A navy blazer is an autumn must-have. Layer it over a cable-knit sweater and mini skirt to achieve a classic preppy look that feels fresh and modern.
Edgy Twist: Leather Jacket & Pleated Skirt Combo
Blend prep with an urban twist by pairing a pleated skirt and white shirt with an oversized leather jacket. This outfit is perfect for mixing traditional and edgy fall styles.
Plaid Dress Perfect for a Coffee Date
For a cozy coffee date outfit, style a plaid dress with black tights and chunky lace-up boots. A chic beret tops off the look, bringing a hint of Parisian charm to your autumn wardrobe.
Weekend Ready: Beige Sweater & Mini Skirt Pairing
For a timeless preppy look, layer a beige cable-knit sweater over a white shirt and mini skirt. This cozy combination is perfect for fall weekends or casual outings.
Retro Inspiration: Black Blazer & Grey Sweater Combo
This black blazer and grey sweater combination looks like it’s straight out of a 90s prep movie. Wear with loafers or brogues to fully embrace that classic fall vibe.
Fall Perfection: Navy Jacket & Plaid Skirt Pairing
A plaid skirt paired with a navy jacket is quintessential preppy. Complete the look with loafers and socks, and you’re ready for a day of autumn adventures.
Light Academia Aesthetic: Cream Knit & Belted Trousers
Channel light academia with a cream knit sweater and belted trousers. The brown accessories add a subtle touch of warmth, making this look ideal for crisp fall days.
Modern Prep: Gray Vest & Wide-Leg Trousers
Layering a gray vest over a crisp button-down creates a clean preppy look, but the wide-leg trousers add a modern twist, balancing traditional style with contemporary flair.
Effortless Autumn: Plaid Skirt Paired with Loafers
Nothing says fall prep quite like a plaid skirt and cable-knit sweater combo. Brown tones and loafers give this outfit an effortless autumn vibe perfect for strolling through the leaves.
Timeless Stripes: Striped Shirt & Sweater Vest Combo
A striped shirt is a preppy essential. Layer it with a brown sweater vest and tailored black pants for a polished yet laid-back fall outfit that’s both timeless and effortlessly chic.
Fall Fashion Staple: Sweater Vest & Mini Skirt Combo
The classic cable-knit sweater vest layered over a white shirt meets the mini skirt for a playful take on preppy fall fashion. Complete the look with penny loafers or oxfords for an easy fall-ready ensemble.
Warm Rust Sweater & Plaid Skirt Combo
For a stylish autumn vibe, team up a cozy rust-hued sweater with a trendy plaid mini skirt. Finish the outfit with beige knee-high boots and a matching knit beanie for a chic seasonal look. A sleek brown crossbody bag adds the perfect blend of practicality and style.
Cozy Plaid Jacket Fall Ensemble
Elevate your fall wardrobe with a cozy plaid jacket layered over a warm-toned turtleneck. Pair it with high-waisted jeans and trendy ankle boots for a classic autumn outfit. Add a stylish hat to complete this effortlessly chic look.
Mustard Suede Jacket & Casual Fall Vibes
Opt for a mustard suede jacket over a white crop top, matched with high-waisted skinny jeans for a laid-back fall outfit. Finish off the look with black ankle boots and a sleek handbag for a casual yet polished feel.
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These 28 preppy fall outfits are not only Pinterest-worthy but also perfect for navigating cooler weather in style. Which look is your favorite? Drop your thoughts in the comments, and don’t forget to share this post on social media!
