fall is hands-down the best season for fashion. You’ve got layering, cozy fabrics, rich colors... and of course, that crisp breeze that makes a cable-knit sweater feel like a hug from a hot latte. But if you’re aiming for a timeless, put-together look without looking like you tried too hard, the preppy vibe is where it’s at.
Now, I’ve been riding the preppy wave since my college days (picture oversized blazers, penny loafers, and more stripes than a sailor’s closet). So believe me when I say: you don’t need a yacht club membership to rock these looks.
Ready to channel your inner Blair Waldorf or Jake from J.Crew? Let’s do this.
1. The Classic Cable-Knit Sweater + Button-Down Combo
Let’s start strong. You literally cannot go wrong here.
Why It Works:
- It screams effortless prep.
- Layers well with coats, scarves, or a PSL in hand.
- You can go neutral or bold—totally your call.
Style tip: Let the collar and cuffs of your button-down peek out for that I-woke-up-this-chic finish. Bonus points if you add a brooch or monogram pin. Yes, we’re being that extra.
2. Blazer + Turtleneck + Slim Trousers
So you want to look smart, warm, and ready to conquer the world (or at least the group chat)? Say hello to your new uniform.
Outfit Formula:
- Structured blazer (navy, camel, or plaid—your choice)
- Lightweight turtleneck underneath
- Tailored pants—not jeans, not joggers, but that sweet in-between
This combo = autumn boss energy. I wore this to a fall brunch once and even the waiter complimented me. FYI, that never happens.
3. Plaid Skirt + Chunky Knit + Knee-High Boots
Let’s hear it for the “private school chic” moment. Plaid skirts have been doing the most for decades—and somehow, they still work every single fall.
Key Details:
- Tuck in your knit for some shape.
- Go for wool or tweed textures—they scream fall.
- Add tights if it’s chilly or if you want to feel like you’re in a Gilmore Girls reboot.
And yes, twirling in this outfit is basically required. Don’t fight it.
4. Cardigan + Oxford Shirt + Straight Jeans
Honestly? This one’s ridiculously easy—and that’s why I love it.
Here’s the deal:
- Choose a fitted or oversized cardigan (both work, trust me)
- Layer it over a crisp oxford shirt (blue or white is the classic move)
- Pair with straight-leg jeans—no rips, no wild washes, just clean and classic
Add loafers or ballet flats, and boom—you’re out the door in 5 minutes looking like you own a vineyard in Connecticut.
5. Sweater Vest + White Shirt + Pleated Skirt
Sweater vests had their moment—and guess what? They’re still here.
Why You’ll Love It:
- They give instant “back-to-campus” vibes.
- Super layer-friendly (and we love a good layer)
- Pleated skirts keep the look sharp and flirty at the same time
Pro tip: Go for neutral vests to keep it polished, or try argyle if you want to go full prep nostalgia.
6. Trench Coat + Loafers + Cropped Trousers
If your goal is “I own 14 leather-bound books and a mysterious backstory,” this is it.
The Staples:
- Camel trench coat—a non-negotiable
- Polished loafers (bonus points for tassels or a chunky sole)
- Cropped trousers to show off those ankles (and socks—if you’re feeling quirky)
You’ll look like you stepped out of a fall fashion catalog. Honestly, not mad about it.
7. Polo Shirt + Blazer + Corduroys
A little sporty, a little sophisticated. Think golf club, but make it fashion.
Mix and Match:
- Fitted polo—navy, forest green, or burgundy = chef’s kiss
- Corduroy pants in tan or olive for that fall texture
- Blazer on top for a tailored, clean finish
And yes, you can totally steal your dad’s old cords. Just don’t tell him.
8. Wool Mini Dress + Tights + Loafers
This one’s basically your shortcut to looking like an autumnal goddess with minimal effort.
Here’s the magic:
- Look for structured mini dresses in plaid, houndstooth, or solid jewel tones
- Pair with black tights for warmth and polish
- Finish with chunky loafers or Mary Janes
Add a headband if you’re feeling bold. Honestly, live your Clueless fantasy.
9. Henley + Vest + Chinos
Guys (and anyone channeling menswear vibes), this one's for you.
Why It Works:
- Henley shirts are casual but grown-up
- A quilted vest or puffer gives you that functional, preppy edge
- Chinos keep it sharp—go for caramel, khaki, or even forest green
Wear this apple-picking or leaf-peeping and prepare for unsolicited compliments. You’ve been warned.
10. Tweed Blazer + Turtleneck Dress
A tweed blazer walks into a bar... and immediately becomes the best-dressed in the room.
Style Hack:
- Throw a tweed blazer over a turtleneck knit dress
- Add knee-high boots and maybe a leather belt for shape
- Top it off with gold accessories for a little polish
This one is my go-to when I want to look like I have my life together (even if I totally don’t).
11. Striped Rugby Shirt + High-Waisted Jeans
Rugby shirts are criminally underrated, IMO. They’re sporty, structured, and give major Ivy League energy without being stiff.
Why You’ll Want One:
- They’re cozy but pulled together
- Bold stripes = instant visual interest
- Pair with high-waisted jeans and a crossbody bag and you’re done
12. V-Neck Sweater + Collared Shirt + Pleated Trousers
Last but not least—this one’s giving autumn CEO and I am here for it.
The Look:
- Pick a deep V-neck sweater (navy, burgundy, grey = yes)
- Layer over a button-down with a pop of collar
- Tuck into pleated trousers for that timeless, I’ve-had-my-coffee look''
Add loafers and a leather satchel and you’re basically unstoppable.
Final Thoughts: Preppy Isn’t Just a Vibe—It’s a Lifestyle
And there you have it: 12 classic preppy fall outfits that never go out of style. Whether you're headed to class, brunch, a cozy bookstore, or literally just walking your dog in the park—you can absolutely look like you stepped off a Ralph Lauren runway (minus the terrifying price tag).
The trick? Keep it classic, mix textures, and don’t be afraid to lean into the crisp, clean aesthetic. Honestly, a little effort here goes a long way. Trust me—I’ve worn a plaid skirt and oversized sweater combo so many times, it practically has its own fall tradition by now.
So what’s your go-to fall preppy look? Got a fave from this list? Or maybe a fashion horror story involving argyle socks? Either way—spill in the comments or send this to your bestie who still thinks leggings count as pants.
Catch you at the apple orchard 🍎