We’re done with preppy summer outfits, and now it’s time to shift gears into fall mode. Think plaid skirts, cable knits, blazers, and layers on layers. Whether you’re channeling Ivy League vibes or cozy autumn academia, these preppy fall outfits will have you looking polished and ready for cooler days.
1. Cable Sweater & Khakis
Cable-knit sweaters are preppy essentials. Layer over a crisp collared shirt and pair with pleated trousers to lock down that nostalgic, 90s collegiate fall look.
Classic prep but with a kick. The white pleated skirt brings out that preppy tennis club vibe, while knee-high boots toughen it up for cooler weather.
3. Plaid Vest & Khakis
The plaid vest brings major old-money, boarding school energy. Pair it with khaki trousers and a button-down, and you’ve got a foolproof fall look.
SEE ALSO: Old Money Outfit Inspo You Need This Fall
4. Cardigan & Plaid Skirt
This combo is giving serious prep school nostalgia. The white cardigan is soft and easy, but that plaid mini and a headband? Total Blair Waldorf energy.
5. Green Sweater & Khakis
This green sweater and khaki pants combo is giving serious dark academia vibes. Keep it simple but throw in a bold bag, and you’ve just made preppy look like a power move.
6. Matching Blazer & Shorts
Shorts in fall? Yeah, we’re doing it. Black blazer and a white shirt up top, sheer black leggings down low, chunky loafers on the feet. Perfect for that fall-in-the-city look.
7. Blue Shirt & Plaid Pants
Plaid and button-downs—simple but not basic, it’s heritage prep done right. Tuck that shirt in, grab your coffee, and look like you actually planned your life today.
8. Sweater Vest & Black Trousers
Sweater vests are having a major moment, and layering one over a white collared shirt is non-negotiable for fall. If you’re going for that old-school, academic vibe, this is the ’fit.
9. Tweed Blazer & Mini Skirt
Tweed is preppy DNA. Throw it over a white button-down and mini skirt, add some loafers, and you’ll look like you just walked off a Ralph Lauren ad.
10. Beige Cardigan & Plaid Pants
Cardigans + plaid trousers = instant Ivy League vibes. Beige knit keeps it soft, plaid brings the structure and loafers add that rich-kid-on-autumn-break look.
You can’t go wrong with a navy blazer in the fall—it’s a preppy essential. The cable-knit sweater underneath gives that cozy, collegiate feel, and the mini skirt keeps the look modern.
12. Leather Jacket & Pleated Skirt
This is where prep meets downtown cool. The pleated skirt and white shirt are the prep classics, but the oversized leather jacket throws some curveballs into the mix.
13. Beige Sweater & Mini Skirt
You can’t get more classic than a cable-knit sweater layered over a crisp white shirt. The mini skirt makes it fresh, but it’s still super academia vibes. Wear it with loafers or brouges and call it a day.
14. Black Blazer & Grey Sweater
Black blazer over a gray sweater and a white shirt and you’re basically auditioning for a 90s prep revival movie. Pair it with brogues or loafers, and you’re ready to own fall in every possible way.
Plaid skirts = preppy fall perfection. Add a navy jacket and loafers, and you’re basically living that East Coast prep life. Socks with loafers? Obviously.
16. Cream Knit & Belted Trousers
Cream knits and belted trousers and you’re channeling fall light academia. The brown accessories tie it together in a subtle but effective way—classic, clean, and perfect for fall.
17. Gray Vest & Wide-Leg Trousers
A gray vest layered over a crisp white button-down is classic prep, but those wide-leg trousers? That’s a power move. A modern spin on the whole vintage prep aesthetic.
18. Plaid Skirt & Loafers
This plaid skirt and cable-knit sweater combo is like a preppy autumn postcard. The brown tones feel like the first week of fall, and those loafers are a preppy must.
SEE ALSO: Brown Outfit Ideas to Rock This Fall
19. Striped Shirt & Sweater Vest
Striped shirts are a preppy staple. Add a brown sweater vest and some black tailored pants, and you’ve got a clean, classic fall look that doesn’t need any extra.
20. Sweater Vest & Mini Skirt
Cable-knit sweater with a white shirt is classic autumn academia. Throw on a mini to balance those layers, add some penny loafers or oxfords and you’re ready for a fall fashion moment!
There you go—preppy fall looks ready for anything. Drop your faves in the comments and don’t forget to share this post on your socials.
