fall fashion is elite. The layers, the textures, the warm tones—it’s basically fashion’s Super Bowl. And if you’ve ever looked at someone and thought, “How do they look so effortlessly put-together?”—spoiler alert: it’s probably a preppy fall outfit doing the heavy lifting.
I’ve been obsessed with preppy style for years. Like, give me a plaid skirt and a chunky knit and suddenly I think I go to Yale. 😂 So whether you’re new to the preppy vibe or just looking for a few new ways to style what’s already in your closet, I’ve got you covered.
Ready to channel your inner Blair Waldorf with a PSL in hand? Let’s get into it. 🍁
1. Plaid Mini Skirt + Oversized Sweater = The MVP of Fall
Let’s kick things off with a classic. A plaid mini skirt paired with a cozy oversized knit never misses.
Why It Works:
- The plaid adds the preppy edge.
- The sweater balances it out with comfort.
- Boots, loafers, or even sneakers—this outfit plays well with others.
IMO, it’s the perfect “I tried but didn’t try” outfit. Bonus points if you toss on some knee-high socks and a structured bag.
2. Cable Knit Sweater + Corduroy Pants
Two words: texture heaven.
Corduroy just screams fall (I mean, can you even wear it in summer without melting?). Pair it with a chunky cable knit sweater, and suddenly you’re giving major Ivy League energy—even if your weekend plans include zero textbooks.
Styling Tips:
- Stick to warm neutrals: beige, rust, olive.
- Tuck in the front of the sweater to give shape.
- Add a belt for a polished finish.
3. Blazer Over... Literally Anything
You know that one blazer that makes you feel like you own a yacht? Yeah, wear that.
Blazer Pairing Ideas:
- Over a turtleneck and jeans.
- With a skirt and tights.
- Thrown on top of a button-down dress.
FYI: A structured blazer can turn even the most basic outfit into a whole moment.
4. Button-Down Shirt + Sweater Vest Combo
This one’s a little “professor chic,” and I’m 100% here for it.
Why You'll Love It:
- It layers well without the bulk.
- It gives prep school realness in the best way.
- Works with jeans, trousers, or a pleated skirt.
Don’t sleep on the sweater vest. It’s not just for your grandpa anymore. 🙂
5. Tweed Mini Dress + Turtleneck Layer
This outfit? She’s classy. She’s cute. She’s ready to book brunch at the country club.
Style It Like This:
- Add a long-sleeve turtleneck underneath for warmth.
- Layer with tights and loafers.
- Finish with a structured coat or trench.
And let’s be honest—tweed just feels expensive, even if it’s $40 off Amazon. Win-win.
6. Pleated Midi Skirt + Slim Fit Turtleneck
Okay, pleated skirts aren’t just for tennis anymore.
Why It’s a Fall Favorite:
- Super feminine, but still structured.
- Easy to layer with a coat, cropped jacket, or scarf.
- Looks fire with ankle boots or loafers.''
Add a crossbody bag and a slicked-back bun, and you’re basically that girl.
7. Monochrome Neutrals (Beige on Beige)
Nothing says “I have my life together” like a head-to-toe neutral outfit.
Try This Combo:
- Beige slacks or wide-leg trousers.
- Cream turtleneck or crewneck sweater.
- Camel coat layered on top.
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Trust me, it’s giving “quiet luxury” vibes—without the quiet price tag. 😉
8. Argyle Sweater + Straight Leg Jeans
Yes, argyle is back, and it’s not just hanging around your dad’s golf wardrobe.
Make It Modern:
- Choose chunkier knits over thin ones.
- Keep the colors muted or pastel.
- Style with vintage-wash jeans and loafers or platform sneakers.
TBH, I was hesitant about argyle for a while, but now I’m kinda obsessed.
9. Layered Collared Shirt + Crewneck Sweatshirt
Ever seen those girls who look like they’ve mastered “casual cute” in a single glance? This is their go-to.
Styling Recipe:
- Crisp white button-up shirt (collar peeking out).
- Oversized crewneck sweatshirt on top.
- Add leggings or a pleated skirt depending on your vibe.
Finish it off with white ankle socks + loafers for maximum prep.
10. Trench Coat + Anything, Honestly
If fall had an official uniform, the trench coat would be it.
Outfit Combos That Slap:
- Over denim and a knit sweater.
- With a dress and tights.
- Even with sweatpants and sneakers (yes, really).
Pro tip: Go for a slightly oversized cut to give it that effortless European feel.
11. Preppy School Uniform Vibes (Without the Homework)
Think pleated skirt, long socks, cardigan, and Mary Janes. Done right, it’s cute—not costume-y.
Quick Do’s:
- Keep it subtle—skip the full blazer + tie combo.
- Choose soft fabrics and modern colors.
- Keep accessories minimal and clean.
You’re going for cool alumni, not class president. 😏
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12. Varsity Jacket + Mini Skirt Combo
The varsity jacket is sporty and stylish. It’s like the “cool girl” version of prep.
Styling Ideas:
- Pair with a neutral mini skirt.
- Add a fitted tee or cropped sweater underneath.
- Sneakers? Yes. Knee-high boots? Also yes.
This outfit kinda makes you feel like you're starring in a Netflix teen drama. No shame.
13. Loafers with Everything
Okay, not technically an outfit—but loafers deserve their own spotlight.
Why They’re a Must:
- They add instant prep points to any look.
- Work with jeans, skirts, dresses, you name it.
- Comfortable and cute? Say less.
Platform loafers are especially on-trend this season. Add chunky socks or tights, and you’re golden.
14. Preppy Athleisure (It Exists, Trust Me)
Not all preppy fall outfits require skirts and stiff collars. Enter: preppy athleisure.
Outfit Formula:
- Crewneck sweatshirt with school or country club logo.
- High-waisted leggings or bike shorts.
- Add a polo cap and clean sneakers.
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This is my go-to when I want to look like I might go to Pilates... but really I’m just grabbing overpriced coffee.
15. Sweater Dress + Riding Boots
Rounding it out with a fall classic: the sweater dress.
Best Pairings:
- Knee-high riding boots (bonus points for leather).
- A waist belt to cinch in the silhouette.
- Add a trench or long cardigan for chillier days.
It’s polished, cozy, and perfect for everything from work to weekend brunch.
Final Thoughts: Are You Fall-Ready or What?
If you’ve made it this far, congrats—you’re basically a preppy fall fashion pro now. Whether you’re team plaid skirt or loyal to the blazer life, these outfits will boost your style faster than a PSL boosts serotonin.
Fashion should be fun, and fall gives us a legit excuse to layer like it’s our job. So play around, mix classics with modern twists, and don’t be afraid to pretend you go to an Ivy League school for the aesthetic. I mean, who’s gonna stop you? 😉
Now go forth and conquer the sidewalks like they’re your runway. And hey, tag me if you rock any of these looks—I need to see. ✨