fall is the season for preppy girls to shine. Between pumpkin patches, cozy café runs, and every excuse to layer (hello, sweater weather!), autumn is basically our personal runway. If you're like me, you've probably got a fall bucket list longer than your Starbucks order. But the real question isn’t what to do—it’s what to wear while doing it. 😉
So, grab your PSL, fluff your favorite cable-knit sweater, and let’s run through 10 preppy-perfect outfits for every fall activity you’ve got lined up. Bonus: You’ll look chef’s kiss amazing in every Insta pic.
1. Pumpkin Patch Chic
Let’s start with a classic. I mean, did fall even happen if you didn’t visit a pumpkin patch?
What to Wear:
- Plaid flannel shirt (bonus points if it’s oversized)
- Dark skinny jeans or riding pants
- Hunter rain boots (because pumpkin patches = mud. Just sayin’)
- Quilted vest in navy or hunter green
- Top it off with a cable-knit headband or a monogrammed baseball cap
Why it works: You look effortlessly adorable and you’re dressed to climb hay bales without flashing the entire crowd. Win-win.
2. Apple Picking Preppy
Apple picking is basically cardio disguised as a photo op. You’ll be stretching, climbing, and probably low-key competing for the best-looking fruit. Don't lie—we all do it.
What to Wear:
- Striped Breton top (because French-girl chic always wins)
- High-rise denim skirt with black tights
- Bean boots for traction and style
- Barbour waxed jacket if it’s chilly
Pro tip: Tie a silk scarf around your ponytail or bag handle. It’s cute, it’s practical, and it screams, “Yes, I absolutely read Town & Country.”
3. Fall Foliage Hike (aka a Walk with Purpose)
You’re outdoorsy—but make it preppy. Fall hikes are perfect for showing off your Patagonia collection and pretending you didn't almost twist your ankle on that wet leaf. 😬
What to Wear:
- Fitted Patagonia Better Sweater fleece
- Lululemon Align leggings (because comfort = key)
- Nike trail shoes or hiking boots in a neutral color
-
Baseball cap with your alma mater (we all have one)
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Why it slaps: You’re functional and fashionable. And yes, your “hiking look” deserves its own Reel.
4. Tailgate Ready
Even if you don’t know what’s happening on the field, you better believe your outfit is game-day-ready.
What to Wear:
- Plaid skirt or corduroy mini in your school colors
- Oversized cable-knit sweater (borrow from your boyfriend... or just pretend)
- Knee-high socks and loafers or Chelsea boots
- Add a wool varsity jacket for the full “I might be in a sorority” look
FYI: A crossbody bag is non-negotiable—you need hands free for snacks and selfies.
5. Coffee Date Cutie
Whether it’s a date-date or just catching up with your bestie, your coffee outfit should say, “I just threw this on,” while looking suspiciously curated. You know the vibe.
What to Wear:
- Turtleneck bodysuit in a neutral tone
- High-waisted straight-leg jeans
- Plaid blazer (because structure = sophistication)
- Loafers or ballet flats with a fun pattern
- Optional: Silk scrunchie around your wrist for that touch
Why it works: It’s clean, polished, and you’ll feel put-together even if your latte spills. (Been there.)
6. Farmers Market Fashion
This is your time to channel a 90s rom-com heroine. You're romanticizing your life while sniffing apples and dodging toddlers with sticky fingers.
What to Wear:
- Midi-length floral dress layered with a longline cardigan
- Leather riding boots or suede booties
- Crossbody satchel to hold your artisan honey and overpriced sourdough
- Top it off with a beret or floppy wool hat if you're feeling extra
Hot take: You’ll blend right in with the gourds and vintage mason jars. In a good way.
7. Bonfire Night Babe
Crisp air, s’mores, oversized blankets—aka, peak fall vibes. And yes, you can look cute while sitting by the fire.
What to Wear:
- Oversized crewneck sweatshirt (bonus if it’s your hometown or fav college)
- Leggings or fleece-lined joggers
- Wool socks and UGGs (don’t come for me—they’re back and better than ever)
- Bring a blanket scarf big enough to double as an actual blanket
IMO: You don’t need to try hard here. Cozy > couture.
8. Fall Picnic Look
Okay, not all fall days are freezing. On those rare sunny afternoons, a picnic in the park is the chef’s kiss of preppy plans.
What to Wear:
- Cable-knit sweater tucked into a tweed mini skirt
- Opaque tights for warmth (and sass)
- Ankle boots with a small heel for the aesthetic
- Carry a vintage-style wicker bag—yes, even in fall
Rhetorical Q: Can you even call it a picnic without brie, grapes, and aesthetic vibes?
9. Friendsgiving Festivities
Friendsgiving = stretchy pants, but make them fashion. You're eating and posing, so balance is key.
What to Wear:
-
Knit sweater dress (so comfy, so cute)
- Knee-high leather boots
- Gold hoops or a pearl headband—keep it polished
- A belt to cinch the waist (and hold you together emotionally when your pie flops)
Honest Moment: You’ll probably spill cranberry sauce on something. Just go with it.
10. Library Study Sesh (Yes, That Counts)
Even your “quiet girl fall” moments deserve style. Studying, journaling, Pinteresting your dream closet—it all requires the look.
What to Wear:
- Oxford shirt layered under a sweater vest
- Pleated skirt or plaid pants (preppy uniform vibes)
- Loafers or Mary Janes
- A pair of blue light glasses for ✨aesthetic stress✨
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Pro tip: Even if you’re only reading Colleen Hoover, the outfit still slaps.
Final Thoughts: Dress the Season, Not the Weather (But Actually, Both)
Fall is the preppy girl’s playground. With the right outfit, even the most basic activity (cough, leaf-peeping) turns into a mini fashion moment. You don’t need to reinvent the wheel—just remix your staples, add a touch of personality, and own whatever cozy chaos autumn throws your way.
So, what’s first on your fall bucket list? And more importantly—what are you wearing? 😉