Okay, fashion besties—let’s talk about fall and preppy style. Because, honestly? It’s the comeback no one saw coming (and I’m so here for it).

From pleated skirts and chunky loafers to cozy cable-knit sweaters and blazers that scream academia-core, preppy fashion is officially dominating Fall 2025. It’s the kind of look that makes you want to sip coffee at a corner café and pretend you’re the main character in a collegiate rom-com. ☕

So whether you’re heading to brunch, class, or a pumpkin patch photo shoot, these 18 preppy fall outfits will have you looking put-together but chill. Let’s dive into the looks every stylish girl is rocking this season.

1. The Classic Sweater Vest Combo

Sweater vests are basically the backbone of preppy fashion—and they’re not going anywhere.

Pair a checkered or argyle sweater vest with a crisp white button-up and pleated mini skirt. Add loafers, and boom—you’re giving elite private school energy in the best way possible.

Style tip: Toss on an oversized blazer if it’s chilly, and suddenly you’re “that girl” walking across campus like it’s a Vogue shoot.

2. Plaid Skirt + Oversized Knit

If fall had a uniform, this would be it.

A plaid skirt with an oversized knit sweater is cozy, classic, and totally Pinterest-core. The mix of structured and slouchy makes it effortlessly chic.

Pro tip: Balance proportions—tuck in the front of your sweater or belt it for definition.

Would I wear this for every coffee run in October? 100%.

3. Cream Cable-Knit Sweater + Wide-Leg Trousers

The “rich but relaxed” vibe in one outfit.

A cream cable-knit sweater tucked into wide-leg trousers (bonus if they’re beige or camel) is understated luxury. Add gold hoops and a leather crossbody, and suddenly you’re radiating quiet confidence.

Why it works: The neutral palette keeps it classy while the fit screams effortless preppy sophistication.

4. Mini Skirt + Knee-High Boots

This one’s giving Gossip Girl, but make it fall 2025.

A mini skirt, knee-high boots, and a fitted turtleneck are an unbeatable trio. You’ll look polished without feeling overdressed.

Styling inspo:

• Add a trench coat for an academic-core twist.
• Go for suede or leather boots for texture.

It’s cute, timeless, and—let’s be honest—a little flirty.

5. Blazer + Denim Moment

Who said preppy has to mean formal?

A tailored blazer over your favorite straight-leg jeans strikes that perfect balance between smart and casual. It’s the outfit for fall dinners, work events, or coffee catch-ups.

Style idea: Layer with a white tee or striped top for Parisian prep vibes.

Would I wear this on repeat? Probably until someone stages an intervention.

6. Monochrome Neutrals

Minimalist girlies, this one’s for you.

Wearing one color head to toe (think beige, camel, or taupe) is the quiet luxury aesthetic we’re all obsessed with. It’s clean, cohesive, and ridiculously photogenic.

Pro tip: Play with layers and fabrics—mix knits, wool, and leather to keep things interesting.

7. The Schoolgirl Chic Look

If the words “Blair Waldorf” make your heart flutter, this one’s your go-to.

Think collared blouse, pleated skirt, and Mary Janes—aka the perfect nod to Y2K prep with a modern twist.

How to style:

• Layer a cropped cardigan or fitted blazer.
• Add a headband or ribbon for bonus preppy points.

It’s giving Upper East Side, but you actually have taste. 😉

8. Turtleneck + Midi Skirt

A total fall classic that never disappoints.

A fitted turtleneck tucked into a wool or corduroy midi skirt screams elegance without trying. It’s preppy, practical, and super flattering on every body type.

Finish the look: Pair with ankle boots or loafers for a polished finish.

Would I wear this to a gallery date? Without a doubt.

9. Argyle Everything

The argyle pattern is the unofficial logo of preppy style.

Rock it on a cardigan, vest, or skirt for an instant throwback look that still feels 2025-fresh. Keep the rest of your outfit simple—neutral trousers or a pleated skirt will do the trick.

It’s bold but classy, and honestly, it deserves a moment.

10. The Varsity Jacket Vibe

You don’t need to be on a team to score this look.

A varsity jacket layered over a basic tee and mini skirt gives that cool, effortless prep vibe. It’s playful, nostalgic, and perfect for casual fall hangs.

Bonus tip: Pair with white sneakers and chunky socks for a 90s-meets-Y2K twist.

Would I wear this to a football game or fall fair? You know it.

11. Collared Dress + Loafers

Simple, sweet, and preppy perfection.

A collared mini dress (bonus points if it’s in a structured fabric) paired with chunky loafers or Mary Janes gives major fall charm. Add knee socks or tights for warmth and an extra dose of cute.

It’s giving “I read fashion magazines for fun and also have a killer skincare routine.”

12. Blazer Dress Moment

This one is for the power-prep girlies.

A structured blazer dress paired with knee-high boots or loafers takes prep to boss-level. It’s the perfect outfit for date nights, events, or any time you want to feel unstoppable.

Style inspo: Go monochrome with gold jewelry for that ultra-polished finish.

Would I wear this to a rooftop dinner? Oh, absolutely.

13. Striped Sweater + Mini Skirt

You can’t go wrong with nautical-inspired stripes for that timeless preppy touch.

A navy-and-white striped sweater tucked into a neutral mini skirt is effortlessly chic. Add a trench coat, and you’re officially ready for pumpkin spice season.

Pro tip: Keep accessories simple—small hoops, a leather tote, and maybe a beret (if you’re feeling French).

14. Rugby Shirt Revival

Yep, the rugby shirt is back—and she’s cuter than ever.

This old-school prep piece looks adorable with pleated skirts, high-waisted jeans, or even wide-leg trousers. It’s sporty but still chic, especially when half-tucked.

Why it slays: It’s the perfect mix of “I love country clubs” and “I shop vintage.”

15. Layered Knits on Knits

If you’re a layering lover, this is your moment.

Pair a turtleneck under a crewneck sweater and layer with a trench coat or wool vest for major fall sophistication. It’s cozy, elevated, and totally preppy-core.

Color palette tip: Stick to neutrals, olives, or muted browns for that fall-ready vibe.

16. Pleated Trousers + Button-Up

It’s giving “smart prep meets boss energy.”

Pleated trousers and a crisp white button-up are fall staples for a reason. Add a belt, loafers, and maybe a wool coat, and you’ve got a look that works for work, class, or brunch.

Would I wear this on a Monday? Probably—it’s a power move disguised as an outfit.

17. Oversized Cardigan + Slip Dress

Preppy meets cozy meets hot girl fall.

Layer a chunky oversized cardigan over a silky slip dress for the ultimate day-to-night vibe. Add tights and loafers to make it autumn-appropriate.

Why it’s perfect: It blends preppy elegance with that slightly undone edge that keeps it from looking too polished.

18. Matching Tweed Set

We’re ending strong with the ultimate preppy staple: tweed.

A matching tweed set (think mini skirt + cropped jacket) is chic, timeless, and screams “fashion girl autumn.”

Style inspo:

• Pair with knee-high boots or heeled loafers.
• Add pearl earrings or a quilted bag for extra flair.

Would I wear this for every fall brunch? Absolutely—it’s giving Clueless meets Emily in Paris. 💅

🍁 Final Thoughts

Preppy fashion has officially evolved—it’s no longer stiff or “too proper.” In 2025, it’s all about mixing classic staples with modern silhouettes and a touch of main character energy.

Whether you’re into the academic-core aesthetic or just love a good plaid skirt moment, these 18 preppy fall outfit ideas will make your wardrobe feel fresh, chic, and totally on-trend.

So tell me—which one are you trying first? The blazer dress? The plaid mini and boots? Or maybe the varsity jacket moment?

Whatever your pick, remember: preppy isn’t about perfection—it’s about confidence, comfort, and a killer pair of loafers. 😉