10 Must-Have Apple Picking Outfit Fall Casual Plus Size Looks That Are Cute & Comfy
There’s something truly magical about fall—the crisp air, the cozy layers, and of course, apple picking season. For me, nothing kicks off autumn quite like a stroll through the orchard with a warm cider in hand and the perfect outfit that says, “Yes, I’m ready for fall…and I look good doing it.”
As a fashion content writer and self-professed fall fanatic, putting together this blog post was more than just work—it was a passion project. I spent hours scrolling through Pinterest, browsing lookbooks, and digging through Amazon for the best outfit pieces tailored to plus size women who want to feel confident, cute, and comfortable while apple picking.
So if you’re planning your next weekend adventure to the orchard, keep reading. I’ve pulled together 10 must-have looks that nail the apple picking outfit fall casual plus size aesthetic—with ideas for any weather, from warm early-fall days to crisp, chilly afternoons.
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1. The Classic Denim & Flannel Combo
You can’t talk about apple picking without honoring this timeless duo. There’s something so iconic about jeans and flannel, especially when you’re surrounded by apple trees and golden leaves.
Plus size tip: Look for high-waisted jeans with a bit of stretch to keep things comfortable. Pair them with a soft oversized flannel that hits at the hip. Add ankle boots, and you’ve got a look that’s as practical as it is picture-perfect.
Pro tip: If you’re planning to squat or reach up high for those juicy apples, consider jeans with a flex waistband. Trust me—your body will thank you.
2. Oversized Sweater + Leggings Magic
This outfit is all about being warm and effortlessly cute. A chunky, oversized sweater paired with buttery soft leggings creates that cozy-girl vibe that’s so in this season.
This is my go-to when I know I’ll be doing a lot of walking. It’s functional and flattering, especially with the right accessories (think: knee-high socks and a slouchy beanie).
Why it works for plus size women: The leggings create a sleek silhouette, while the oversized sweater balances proportions beautifully. Plus, this look transitions perfectly from cold weather mornings to warm afternoons.
3. The Chic Shacket Look
What’s a shacket, you ask? It’s the perfect blend of a shirt and a jacket—slightly oversized, usually plaid or neutral-toned, and totally on trend.
Wear it open over a fitted tee and jeans or leggings. Add a beanie or wide-brim hat, and suddenly your apple picking outfit fall casual plus size look is effortlessly chic and layered.
Real-life note: I wore this combo last fall and was shocked at how many compliments I got—not to mention how warm I stayed as the weather cooled down.
4. Sweater Dress + Knee-High Boots
If you’re leaning into the feminine, cozy vibe this fall, a sweater dress is your best friend. Look for styles that cinch at the waist or have a belt for shape. Pair it with leggings or thick tights and knee-high boots for a little drama (the good kind).
Top it off with a long coat or blanket scarf and you’ve got a super cute outfit that keeps you warm without compromising style.
Amazon Fashion Pick #1: Levi’s Plus Size 311 Shaping Skinny Jeans
One of my favorite staples for fall is a great pair of jeans—and these Levi’s shaping skinny jeans are a total game changer. They’re stretchy, flattering, and available in extended sizes.
Why I love it: The waistband doesn’t dig in, and they hug in all the right places. Perfect for sitting on hay bales or posing for your orchard Insta pic.
Shop Levi’s Plus Size 311 Shaping Skinny Jeans on Amazon
Grab these now before fall hits full swing—they’re a must-have for your casual autumn wardrobe.
5. Utility Jacket + Graphic Tee Combo
When it comes to warm early autumn days, you want something light and easy. Enter: the classic utility jacket. It’s structured, flattering, and perfect for layering.
Pair it with a cute graphic tee (maybe one that says “Fall Vibes” or “Orchard Obsessed”) and a comfy pair of jeans. Finish it off with white sneakers or boots.
Style tip: Roll the sleeves for that laid-back, cool-girl vibe.
6. Boho Babe in Layers
If your style leans more relaxed and artsy, this look is for you. Think: long cardigans, breezy tunics, and wide-brim hats. Add a pair of flared jeans or leggings, and you’ve nailed the boho orchard look.
I love layering different textures here—knits, suede, and cotton all together. It creates such a rich, fall-forward aesthetic.
7. Monochrome Neutrals
Want to look effortlessly put-together without overthinking it? Try a head-to-toe neutral look. Creams, tans, or even soft grays look gorgeous against a backdrop of apples and leaves.
A cream sweater + taupe leggings + beige booties? It’s a soft, flattering look that feels luxurious but casual.
8. Puffer Vest + Thermal Base Layers
This one’s for those cold weather orchard days when you still want to look cute but stay warm. A puffer vest keeps your core toasty without overheating, and thermal shirts are perfect layering pieces.
Pair with fleece-lined leggings or rugged jeans and waterproof boots. Trust me, you’ll be glad you dressed for the weather when the wind picks up.
Amazon Fashion Pick #2: Columbia Women's Plus Size Benton Jacket
If you need a cozy, flattering top layer, this fleece jacket is everything. It’s warm without being bulky and comes in gorgeous fall tones like rust and olive.
Why I love it: It layers well over a thermal and under a puffer vest—plus the zippered pockets are actually useful!
Shop Columbia Plus Size Fleece Jacket on Amazon
Snag this for your next orchard day—it’s the perfect mix of fashion and function.
9. Tunic + Moto Leggings
Want to feel like a boss while still being comfy? Try a long, flowy tunic with edgy moto leggings. The texture of the leggings gives them a cool-girl vibe, while the tunic keeps things flattering and easy.
Add combat boots and a layered necklace to complete the look. This outfit works for apple picking, lunch after, and maybe even a casual date night.
Amazon Fashion Pick #3: SATINA High Waisted Leggings for Women – Plus Size
These leggings are a bestseller for a reason. They're incredibly soft, stretchy, and come in tons of colors. The high waistband provides tummy support without being restrictive—ideal for plus size women on the move.
Why I love it: Whether you're apple picking or lounging afterward, these leggings hold up all day.
Shop SATINA Plus Size Leggings on Amazon
These sell out every fall—grab yours while they're still in stock!
10. Summer-to-Fall Transitional Look
Not quite ready to say goodbye to summer? No worries—this transitional look lets you dip a toe into fall fashion without going full flannel.
Start with a lightweight cardigan over a sleeveless blouse and rolled cuff jeans. It’s great for those hot days that feel more like August than October, but still say “I’m here for the apples.”
Add sunglasses and a crossbody bag, and you’re good to go.
Bonus Tips for Your Apple Picking Day
- Bring a small backpack: Keeps your hands free for grabbing apples and cider.
- Layer up: Fall weather is famously unpredictable. A layered outfit lets you adapt easily.
- Wear boots or sneakers: You’ll be walking in grass, mud, or even hay, so heels are a no-go.
- Accessorize wisely: Hats, scarves, and sunglasses add to the aesthetic without overcomplicating your outfit.
Final Thoughts
Creating this blog post was like living through a mini fall fashion fantasy. As someone who lives for sweater weather and orchard vibes, I loved curating these apple picking outfit fall casual plus size ideas for you. Every look is meant to highlight your style, your comfort, and your confidence.
Whether you’re braving cold weather, soaking up the last bit of summer, or simply leaning into your cozy autumn aesthetic, there’s something here for every body and every vibe.
So tell me: Which look are you dying to try first? Tag me on Instagram or comment below—I’d love to see your fall fashion in full bloom.
Happy apple picking, beautiful!