What to Wear? 10 Apple Picking Outfit Fall Casual Combos You’ll Love
Hi there, fall lovers! There’s just something magical about autumn — the crisp air, golden leaves, and of course, apple picking season. If you’re anything like me, you look forward to visiting the orchard every year. But I have to confess: for the longest time, I’d stare at my closet thinking what to wear that would look cute in photos, feel comfy, and handle a full day at the farm.
That’s why I put together this guide filled with apple picking outfit fall casual ideas that I truly believe you’ll love. I had so much fun writing this because it took me down memory lane, recalling my past orchard adventures (and outfit mishaps!). This post is packed with inspiration for women who want to stay chic while embracing the cozy aesthetic of autumn. Let’s dive in!
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1. Classic Jeans + Cozy Knit Sweater Combo
If you ask me, jeans and a knit sweater are the ultimate apple-picking uniform. It’s a timeless pairing that gives off effortless chic vibes. I like to go for high-waisted jeans (bonus points for stretchy denim!) paired with a chunky, oversized sweater.
Style Tip: Do a little French tuck (half-tuck) into your jeans and add a belt to define your waist. This combo keeps you warm without feeling bulky — perfect for those cool orchard mornings that heat up by afternoon.
2. Leggings + Long Plaid Shirt + Vest
When I’m in the mood for maximum comfort (especially if I know I’ll be reaching and stretching to pick apples), leggings are my go-to. Pair them with a tunic-length plaid shirt and a quilted vest, and you’re set!
The vest adds that extra bit of warmth without making you overheat, making this ideal for layering on unpredictable autumn days. And plaid? Nothing screams fall casual aesthetic like a good flannel.
3. Denim Overalls + Striped Tee
There’s something so cute and playful about denim overalls. I wore them to the orchard last fall and got tons of compliments (and adorable pics!). Layer a striped or graphic tee underneath for that modern farm vibe.
On a warm day, roll up the hems of the overalls. On cooler days, throw on a cardigan or tie a flannel shirt around your waist for a pop of color and extra layer if needed.
4. Midi Skirt + Chunky Cardigan
Looking for something a little more feminine? A flowy midi skirt paired with a chunky cardigan strikes the perfect balance between cute and practical. I wore this combo last year on a sunny autumn afternoon, and it felt dreamy walking through the rows of apple trees.
Pick earthy tones or plaid prints for that orchard look. And don’t forget comfy boots — you don’t want to be navigating the farm in heels!
Amazon Product Pick #1: PRETTYGARDEN Women’s Chunky Cable Knit Cardigan
If you’re searching for a cozy layering piece, I can personally vouch for the PRETTYGARDEN Women’s Chunky Cable Knit Cardigan. I’ve worn mine to orchards, farmers markets, and even cozy brunch dates. The knit is soft, and it drapes so nicely over dresses, skirts, or even leggings. Plus, it comes in versatile neutral colors that scream fall.
Grab yours here on Amazon and stay cozy during all your autumn adventures!
5. Utility Jacket + Black Jeans + Scarf
This combo has saved me on chilly orchard mornings! A utility jacket is one of my fall staples — it’s functional, flattering, and pairs beautifully with everything. Add a chunky scarf and black jeans for a polished, chic look.
Pro tip: Choose a jacket with lots of pockets for stashing your phone, chapstick, and even a small snack!
6. Casual Jumpsuit + Booties
When you want something cute and easy, go for a casual cotton jumpsuit. It’s a one-and-done outfit that still looks thoughtful. I wore one to the orchard during an unseasonably hot fall day and was so glad I did!
Add a belt to cinch your waist, and layer a cropped jacket if the temps dip later.
7. Leggings + Tunic Sweater + Blanket Scarf
A classic layered look that never fails. A tunic sweater with leggings gives you full range of motion for all that apple picking action. And the blanket scarf? It’s both a style statement and an emergency wrap when it gets chilly.
Choose a scarf with fall tones — think burgundy, rust, or mustard — to match the autumn aesthetic.
Amazon Product Pick #2: Amazon Essentials Women’s Full-Length Leggings
I can’t tell you how many times I’ve reached for my Amazon Essentials Full-Length Leggings for fall outings. They’re thick enough to not be see-through, soft enough to feel like pajamas, and hold up well after multiple washes. I’ve worn them on orchard trips, pumpkin patches, and even on cozy nights in.
Shop these leggings on Amazon — your wardrobe will thank you!
8. Flannel Shirt + Jeans + Beanie
Probably my all-time favorite look for apple picking. Nothing says fall like a good flannel! I like to size up so I can layer underneath if needed. Throw on a slouchy beanie, and you’re set for the cutest orchard photos.
This is one of those apple picking outfit fall casual ideas that works no matter if it’s warm or cold weather — just adjust your layers!
9. Short-Sleeve Tee + Jeans + Lightweight Jacket
We’ve all had those hot autumn or lingering summer days where fall feels more like August. For those days, a short-sleeve tee with jeans and a lightweight jacket is perfect. You can easily take the jacket off when the sun comes out.
A utility or denim jacket works great here, and you’ll still have that chic farm-ready look.
10. Sweater Dress + Tall Boots
When I want a look that’s equal parts cozy and cute, I reach for a sweater dress. Pair it with tall boots (riding boots or knee-highs work well) and leggings if it’s brisk. Add a belt to give it shape and keep your silhouette flattering.
This look transitions beautifully from orchard to cider tasting at a nearby farm café!
Amazon Product Pick #3: DREAM PAIRS Women’s Knee-High Riding Boots
For footwear that’s stylish and practical for muddy farm paths, I can’t recommend the DREAM PAIRS Knee-High Riding Boots enough. They’re comfy for walking, easy to clean, and look amazing with dresses, jeans, or leggings. I’ve worn mine on rainy orchard days and my feet stayed dry!
Check out these boots on Amazon and step into fall in style!
Extra Tips for Apple Picking Style Success
- Layer smart. What to wear can depend on changing temps — start with a base and add layers you can peel off as it warms up.
- Practical shoes are a must. No stilettos at the farm, please! Think boots or sturdy sneakers.
- Accessorize thoughtfully. Crossbody bags or backpacks keep your hands free for picking.
- Stick to earthy tones. Rust, mustard, olive, and burgundy not only look great for fall — they photograph beautifully against apple trees.
Final Thoughts
Writing this post brought back so many fond memories of apple picking trips over the years — from childhood outings with my family to grown-up farm dates with friends. I hope these apple picking outfit fall casual ideas inspire your next autumn adventure. Dressing for the orchard doesn’t have to be stressful. With these combos, you’ll be comfy, stylish, and ready to fill your basket with fresh apples (and your camera roll with cute photos).
Whether you’re braving cold weather, enjoying a warm fall day, or getting in one last orchard trip before summer fully fades, these outfit ideas will have you looking and feeling your best.