8+ Trendy Preppy Fall Outfits You’ll Love to Wear
In this post, we’ll explore preppy fall fits that every woman should have in her wardrobe. From casual preppy outfits perfect for a laid-back weekend to Diplys preppy outfits that shine at brunch.
Here are some standout looks to inspire your preppy fall wardrobe:
🧥 1. Cable-Knit Sweater + Pleated Skirt
Channel academic charm with a chunky cable-knit sweater (think cream or forest green) paired with a plaid or wool pleated mini. Add knee-high socks and loafers to complete the Ivy League aesthetic.
Style tip: Drape a knit over your shoulders for that layered “I just left the library” vibe.
👖 2. Collared Shirt + Cropped Sweater + Wide-Leg Trousers
Layer a crisp white oxford shirt under a cropped crewneck sweater. Pair with tailored trousers or high-rise chinos. This combo is timeless and effortlessly collegiate.
Bonus points: Add a leather belt and vintage watch for polish.
🧣 3. Turtleneck + Tweed Blazer + Jeans
A fitted turtleneck in camel or navy under a structured blazer gives perfect cozy-meets-smart energy. Choose slim jeans or cords and ankle boots.
Add-ons: A plaid scarf or satchel bag ups the prep factor.
🧵 4. Sweater Vest + Button-Up + Mini Skirt
A preppy staple! Pair a knit vest with a long-sleeve button-up shirt and an A-line mini skirt (think houndstooth or tartan). Finish with loafers or Mary Janes.
Optional: Add opaque tights as the weather cools.
🎓 5. Varsity Jacket + Straight-Leg Jeans + Sneakers
Go classic collegiate with a varsity jacket layered over a long-sleeve striped tee. Pair with straight-leg jeans and sleek sneakers.
Keep it cute: A canvas tote or beanie keeps the look youthful.
Beige Trench Coat + White Turtleneck Sweater + Houndstooth Mini Skirt + Navy Printed Scarf + Brown Leather Satchel + Burgundy Loafers
This stunning outfit combines a chic beige trench coat with a cozy white turtleneck, perfect for layering as the season shifts. The houndstooth mini skirt adds a playful touch, while the navy printed scarf brings a splash of elegance. Don’t forget the stylish brown leather satchel and comfy burgundy loafers to complete your look.
Brown Ribbed Bodysuit + White Ruffled Mini Skirt + Brown Knee-High Boots
This blend of casual preppy outfits fall is not only stylish but incredibly versatile. I love how the combination of the warm brown bodysuit and the playful white ruffled skirt creates a chic contrast, while the knee-high boots add a touch of sophistication.
Black White Houndstooth Sweater Vest + Light Blue Button-Up Shirt + Cream Knit Mini Skirt + Tall White Boots
Embrace the preppy fall aesthetic with this outfit that screams sophistication and sass! The houndstooth vest adds a touch of classic charm, while the tall white boots elevate your ensemble to runway status. Perfect for those crisp autumn days when you want to look cute but also feel cozy enough to tackle the world-or at least your next coffee run.
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Brown Houndstooth Blazer + White Bodycon Dress + Brown Knee-High Boots
The combination of a chic brown houndstooth blazer layered over a sleek white bodycon dress creates a sophisticated silhouette, perfect for any occasion. The brown knee-high boots add a trendy touch, enhancing both comfort and style. This outfit not only looks polished but also keeps you cozy, making it ideal for crisp autumn days spent enjoying coffee with friends.
Navy Pleated Midi Skirt + Cream Sweater Blouse + Black Beret + White Sneakers
A cozy cream sweater blouse tucked into a flowing navy pleated midi skirt. The stylish black beret adds a chic touch, complemented perfectly by a trendy navy handbag. Finish the look with comfortable white sneakers, ensuring you stay fashionable while enjoying those crisp autumn walks. This outfit not only looks great but also offers the comfort needed for a day out.
Yellow Rain Jacket + White Tee + Light Blue Mini Skirt + Red Rain Boots
Preppy fall outfits combine practicality and fashion, making them ideal for seasonal transitions. This outfit features a vibrant yellow rain jacket that brightens up dreary days, a classic white tee for a timeless look, and a light blue mini skirt that adds a playful touch. The red rain boots ensure you stay stylish while keeping your feet dry, and the matching headband completes the look with a chic flair.
Cream Trench Coat + Blush Pink Turtleneck Sweater + Navy Mini Skirt + Plaid Scarf + White Rain Boots
The creamy trench coat paired with a cozy blush turtleneck offers warmth, while the navy mini skirt adds a chic touch. I adore the soft plaid scarf, which not only elevates the style but also provides extra comfort on brisk days.
Plaid Cardigan + Soft White Tee + High-Waisted Denim Shorts + Over-the-Knee Taupe Boots
I love how the cozy plaid cardigan adds a warm touch, while the soft white tee keeps it casual. The high-waisted denim shorts are both chic and comfortable, and those over-the-knee taupe boots? They’re a showstopper.
A navy argyle sweater paired with a brown plaid mini skirt, perfect for casual outings or school events.
Try these preppy fall aesthetic with cozy knits or tailored blazers to reflect your unique style while capturing the essence of the season.
