The preppy style is having a moment this fall with designers like Thom Browne, Lacoste, and Tory Burch putting their spin on classic aesthetic. Iconic pieces like rugby shirts, ties, and pleated skirts are being reimagined with a contemporary twist. The hyper-polished fits from the Met steps in Gossip Girl are updated for today, inspired by Blair Waldorf, the character known for prim prep, cardigans, and headbands, but now with more edge. These must-try autumn looks bring stylish, casually chic outfits that elevate any wardrobe.

During NY Fashion Week, posts, pics, and runways show trending outfits curated by editors, celebrities, and influencers. The FYP is full of curated lists of on-trend fall looks, from sleek and sultry pieces to casually chic skirt outfits. Preppy skirts can be paired with classic tops for Cold Weather Outfits, Warm Outfits, or even a Paris Outfit for a season that blends style, comfort, and modern flair while keeping the preppy spirit alive.

Preppy Fall Outfit Ideas

1. Classic Pleated Skirt

A classic pleated skirt is perfect for fall. Pair it with a fitted sweater or blouse and add a cardigan for warmth. Knee-high boots or loafers make it preppy and stylish. This look works for school, brunch, or a casual day in the city. Accessories like a small bag or scarf add polish and keep the outfit balanced and chic for the season.

2. Rugby Shirt Combo

Combine a rugby shirt with a midi skirt for a timeless preppy look. Tuck in the shirt and add a belt to define the waist. Layer with a cardigan or blazer depending on the weather. Loafers or sneakers complete the outfit. This look is both casual and polished, perfect for autumn walks, coffee with friends, or casual gatherings.

3. Blair Waldorf Look

Inspired by Blair Waldorf, this outfit features a pleated midi skirt, fitted sweater, and statement headband. Add a cardigan or blazer for layering. Loafers or heeled shoes create a polished effect. This preppy look works well for brunch, city strolls, or events where you want to feel stylish yet effortless in fall weather.

4. Chic Autumn Skirt

A chic autumn skirt outfit pairs a flowy midi skirt with a cozy knit sweater. Layer with a light jacket or trench for cooler mornings. Boots or flats add elegance and comfort. Add minimal accessories to keep the look sophisticated. This ensemble works for autumn dates, casual office days, or a stylish weekend outing.

5. Cardigan Layer Outfit

Layer a fitted cardigan over a blouse with a pleated midi skirt for a preppy effect. Tuck the blouse in for a neat silhouette. Pair with loafers or ankle boots. Accessories like a scarf or small bag enhance the fall vibe. This outfit is versatile for school, meetings, or a walk in the park during the season.

6. Sleek Midi Ensemble

A sleek midi ensemble features a high-waist midi skirt and fitted top. Add a blazer or cropped jacket for structure. Loafers or heels keep it polished. This look works well for casual workdays, brunches, or autumn events where you want to feel confident and put together with minimal effort.

7. Preppy Paris Style

For a Parisian preppy style, pair a plaid or checkered midi skirt with a turtleneck or blouse. Add a beret and loafers for the complete look. A trench coat or light jacket works for cooler days. This outfit is perfect for city exploration, coffee outings, or stylish weekend travel in the fall.

8. Tory Burch Inspired

Take inspiration from Tory Burch by pairing a printed midi skirt with a sweater or blouse. Layer with a cardigan or structured jacket. Add flats, loafers, or boots depending on the weather. Accessories like a small crossbody bag finish the polished preppy aesthetic for casual autumn days or events.

9. Layered Cold Weather

For colder days, wear a midi skirt with thick tights, a sweater, and a long cardigan or coat. Boots keep feet warm and stylish. Add a scarf and small bag for practicality. This layered preppy outfit works for autumn walks, school, or coffee dates while keeping cozy and polished.

10. Casual Preppy Look

A casual preppy look pairs a midi skirt with a soft knit sweater and loafers or sneakers. Layer with a light jacket or cardigan for cool weather. Minimal accessories make the outfit easy and comfortable for school, city walks, or weekend brunches without losing style.

11. Edgy Preppy Outfit

Add a twist to preppy style by pairing a midi skirt with a leather jacket or bold sweater. Loafers or boots balance the edge and sophistication. Accessories like a headband or bag keep the look chic. This outfit works for autumn nights out, casual events, or any day you want to feel stylish and unique.

12. Warm Autumn Skirt

Pair a midi skirt with a warm knit sweater for cozy fall days. Add a cardigan or light coat for extra warmth. Knee-high boots or flats complete the outfit. Accessories like scarves and small handbags enhance the preppy vibe while keeping you comfortable during autumn strolls or casual gatherings.

13. On-Trend Skirt Combo

Stay on-trend by combining a patterned midi skirt with a solid sweater or blouse. Layer with a blazer or cardigan. Loafers or ankle boots complete the polished preppy look. This outfit is perfect for events, brunch, or city exploration in the fall while keeping a fashionable edge.

14. Iconic Preppy Pieces

Use iconic preppy pieces like pleated skirts, collared shirts, and cardigans for a timeless fall outfit. Pair with loafers or boots for a polished finish. Accessories like headbands or scarves complete the look. This ensemble works for school, casual outings, or weekend brunches during autumn.

15. NY Fashion Inspired

Take cues from NY Fashion Week by pairing a stylish midi skirt with a sweater or blouse. Add a blazer or trench coat for layering. Loafers or heeled boots keep it chic. This preppy look works for autumn events, city strolls, or casual dinners where style matters.

16. Contemporary Preppy Style

A contemporary preppy style mixes modern pieces with classic skirts. Pair a midi skirt with a fitted sweater or blouse. Layer with a structured jacket or blazer. Loafers or boots complete the look. This outfit is versatile for autumn days, casual office wear, or stylish weekend outings.

17. Sultry Preppy Skirt

For a sultry twist, wear a flowy midi skirt with a fitted knit top. Add a cropped jacket or blazer for shape. Heeled boots or sleek flats polish the look. This outfit works for evening autumn dates, stylish brunches, or casual events where you want a refined yet feminine look.

18. Editors Favorite Outfit

Editors’ favorite fall outfit pairs a midi skirt with a knit sweater and layered cardigan or blazer. Loafers or ankle boots complete the preppy aesthetic. Add a scarf or bag for polish. This ensemble works for fashion-forward autumn outings, city walks, or casual gatherings with friends.

19. Influencer Street Style

Influencer street style features a midi skirt with a turtleneck or blouse. Layer with a leather jacket, trench, or cardigan. Loafers, boots, or sneakers complete the look. Accessories like a crossbody bag enhance the fall outfit. Perfect for city streets, weekend brunch, or casual autumn events.

20. Curated Fall Ensemble

A curated fall ensemble combines a patterned or solid midi skirt with a sweater or blouse. Layer with a blazer or cardigan. Loafers or ankle boots complete the polished preppy aesthetic. Add a scarf or bag to finish the look. This outfit is versatile for autumn workdays, casual outings, or stylish weekend plans.