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Home Cold Weather Style 12 Instagram-Worthy Apple Picking Outfits: Trendy and Orchard Friendly
  • Cold Weather Style
  • Fall
  • Fashion

12 Instagram-Worthy Apple Picking Outfits: Trendy and Orchard Friendly

  • Kara
  • September 16, 2024
  • Contains Affiliate Links

Apple picking season is here!! As a basic fall betch who loves all things apple cider (especially donuts!) scented candles, fresh-baked bikes and pumpkin spiced lattes, I always go apple picking every September.

When it comes to fashion and apple orchards, I’m your gal. In this post I’ve gathered up all the best styles you can shop online right now to wear apple picking, plus photos for inspiration.

Apple picking in the fall

I always travel up to the Sierra Foothills to go apple picking in Apple Hill, the best orchards in California (or, sometimes Sonoma!) Our apple season is September, but yours may run a bit earlier or later depending on where you live – typically September to early October. 

If you’re planning a fall getaway and want to refresh your fall wardrobe, consider a service like Stitch Fix or if you’d prefer to rent clothes – I’ve been testing Nuuly. 

What To Wear For Apple Picking This Fall: Quick Tips

If you’re staring at your closet asking yourself, what do you wear for apple picking? I think the cutest outfits for apple picking are the ones that really go hard on fall vibes. I’m talking cozy sweaters with denim jeans. Gingham dresses with a straw picnic basket. All that basic fall stuff I know you love. 

When styling apple orchard outfits, remember that the orchards will be mostly green with little pops of red. So, whites, light tans, red and orange colors look really nice.

What shoes should I wear for apple picking? A pair of boots is always a good options, or if you’re more comfortable in sneakers, that works too! Just be sure to wear some durable to make your way around the orchard!

Converse Chuck Taylor All Star High Top Sneaker
Converse Chuck Taylor All Star High Top Sneaker
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These are my favorite outfit combos and pieces I look for when styling a cute apple picking outfit:

  • A pair of tall brown boots (these my favorite boots available this season!)
  • Hunter Boots (especially handy on rainy fall days at the orchard)
  • Thrifted straw basket or picnic basket
  • Red gingham dress (paired with a denim jacket)
  • Blanket scarf (that’s also cozy for winter outfits)
  • Plaid or tweed jacket
  • White maxi dress 
  • Overalls (this pair comes in so many sizes!)
  • Flannel shirt 
  • Vintage straight leg jeans (with ankle boots or slide on clogs!) 
Apple Hill Apple picking!
Looking for pumpkin picking outfit ideas? Check out my post here!

12 Apple Picking Outfit Ideas

 
Mini Hoops
 
Everlane Luxe Micro-Rib Long-Sleeve Crew
 
Embracing Autumn Corduroy Pinafore Mini Dress
 
Logan Over the Knee Boot
Mini Hoops
Everlane Luxe Micro-Rib Long-Sleeve Crew
Embracing Autumn Corduroy Pinafore Mini Dress
Logan Over the Knee Boot
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Mini Hoops
Mini Hoops
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Everlane Luxe Micro-Rib Long-Sleeve Crew
Everlane Luxe Micro-Rib Long-Sleeve Crew
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Embracing Autumn Corduroy Pinafore Mini Dress
Embracing Autumn Corduroy Pinafore Mini Dress
Buy Now
Logan Over the Knee Boot
Logan Over the Knee Boot
Buy Now

 
Cotton On Rib Scoop Neck Long Sleeve Top
 
Mini Pencil Skirt
 
Logan Over the Knee Boot
Cotton On Rib Scoop Neck Long Sleeve Top
Mini Pencil Skirt
Logan Over the Knee Boot
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Cotton On Rib Scoop Neck Long Sleeve Top
Cotton On Rib Scoop Neck Long Sleeve Top
Buy Now
Mini Pencil Skirt
Mini Pencil Skirt
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Logan Over the Knee Boot
Logan Over the Knee Boot
Buy Now

 
Levi's Women's Vintage Overalls (Also Available in Plus)
 
Cotton On Rib Scoop Neck Long Sleeve Top
 
Presley Plaid Button Down Top
 
Boston Suede Leather Birkenstocks
Levi’s Women’s Vintage Overalls (Also Available in Plus)
Cotton On Rib Scoop Neck Long Sleeve Top
Presley Plaid Button Down Top
Boston Suede Leather Birkenstocks
Buy Now
Buy Now
Buy Now
Buy Now
Levi's Women's Vintage Overalls (Also Available in Plus)
Levi’s Women’s Vintage Overalls (Also Available in Plus)
Buy Now
Cotton On Rib Scoop Neck Long Sleeve Top
Cotton On Rib Scoop Neck Long Sleeve Top
Buy Now
Presley Plaid Button Down Top
Presley Plaid Button Down Top
Buy Now
Boston Suede Leather Birkenstocks
Boston Suede Leather Birkenstocks
Buy Now

 
Everlane Luxe Micro-Rib Long-Sleeve Crew
 
Madewell '90s Straight Jean
 
Old Navy Canvas Barn Jacket
 
Dolce Vita Reyes Ballet Flats
Everlane Luxe Micro-Rib Long-Sleeve Crew
Madewell '90s Straight Jean
Old Navy Canvas Barn Jacket
Dolce Vita Reyes Ballet Flats
Buy Now
Buy Now
Buy Now
Shop Now
Everlane Luxe Micro-Rib Long-Sleeve Crew
Everlane Luxe Micro-Rib Long-Sleeve Crew
Buy Now
Madewell '90s Straight Jean
Madewell '90s Straight Jean
Buy Now
Old Navy Canvas Barn Jacket
Old Navy Canvas Barn Jacket
Buy Now
Dolce Vita Reyes Ballet Flats
Dolce Vita Reyes Ballet Flats
Shop Now

 
Check Pleated Shorts With Belt
 
Universal Thread Cozy Knit Button-down Cardigan
 
Black Loafers
Check Pleated Shorts With Belt
Universal Thread Cozy Knit Button-down Cardigan
Black Loafers
Buy Now
Buy Now
Shop Now
Check Pleated Shorts With Belt
Check Pleated Shorts With Belt
Buy Now
Universal Thread Cozy Knit Button-down Cardigan
Universal Thread Cozy Knit Button-down Cardigan
Buy Now
Black Loafers
Black Loafers
Shop Now

 
Alice + Olivia Siobhan Vegan Wrap Mini Skirt
 
Revolve Harlow Flannel Shacket
 
Logan Over the Knee Boot
Alice + Olivia Siobhan Vegan Wrap Mini Skirt
Revolve Harlow Flannel Shacket
Logan Over the Knee Boot
Buy Now
Buy Now
Buy Now
Alice + Olivia Siobhan Vegan Wrap Mini Skirt
Alice + Olivia Siobhan Vegan Wrap Mini Skirt
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Revolve Harlow Flannel Shacket
Revolve Harlow Flannel Shacket
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Logan Over the Knee Boot
Logan Over the Knee Boot
Buy Now

 
ZESICA Flowy A Line Tiered Midi Dress
 
Long Bow Crinkle Scrunchie
 
Bolga Handmade Wicker General Basket
ZESICA Flowy A Line Tiered Midi Dress
Long Bow Crinkle Scrunchie
Bolga Handmade Wicker General Basket
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Buy Now
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ZESICA Flowy A Line Tiered Midi Dress
ZESICA Flowy A Line Tiered Midi Dress
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Long Bow Crinkle Scrunchie
Long Bow Crinkle Scrunchie
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Bolga Handmade Wicker General Basket
Bolga Handmade Wicker General Basket
Buy Now

 
Aelfric Eden Cable Knit Sweater
 
Hunter Women's Original Short Rain Boots
 
Madewell '90s Straight Jean
 
Apple Harvest Sweater
Aelfric Eden Cable Knit Sweater
Hunter Women's Original Short Rain Boots
Madewell '90s Straight Jean
Apple Harvest Sweater
Buy Now
Buy Now
Buy Now
Buy Now
Aelfric Eden Cable Knit Sweater
Aelfric Eden Cable Knit Sweater
Buy Now
Hunter Women's Original Short Rain Boots
Hunter Women's Original Short Rain Boots
Buy Now
Madewell '90s Straight Jean
Madewell '90s Straight Jean
Buy Now
Apple Harvest Sweater
Apple Harvest Sweater
Buy Now

 
Utility Denim Jumpsuit
 
Long Bow Crinkle Scrunchie
 
Old Navy Canvas Barn Jacket
Utility Denim Jumpsuit
Long Bow Crinkle Scrunchie
Old Navy Canvas Barn Jacket
Buy Now
Buy Now
Buy Now
Utility Denim Jumpsuit
Utility Denim Jumpsuit
Buy Now
Long Bow Crinkle Scrunchie
Long Bow Crinkle Scrunchie
Buy Now
Old Navy Canvas Barn Jacket
Old Navy Canvas Barn Jacket
Buy Now

 
Converse Chuck Taylor All Star High Top Sneaker
 
Apple Harvest Sweater
 
Levi's Women's Vintage Overalls (Also Available in Plus)
Converse Chuck Taylor All Star High Top Sneaker
Apple Harvest Sweater
Levi's Women's Vintage Overalls (Also Available in Plus)
Buy Now
Buy Now
Buy Now
Converse Chuck Taylor All Star High Top Sneaker
Converse Chuck Taylor All Star High Top Sneaker
Buy Now
Apple Harvest Sweater
Apple Harvest Sweater
Buy Now
Levi's Women's Vintage Overalls (Also Available in Plus)
Levi's Women's Vintage Overalls (Also Available in Plus)
Buy Now

 
Dolce Vita Reyes Ballet Flats
 
Geri Gingham Maxi Dress
 
Betabrand Sloane Jean Jacket
 
Bolga Handmade Wicker General Basket
Dolce Vita Reyes Ballet Flats
Geri Gingham Maxi Dress
Betabrand Sloane Jean Jacket
Bolga Handmade Wicker General Basket
Shop Now
Buy Now
Buy Now
Buy Now
Dolce Vita Reyes Ballet Flats
Dolce Vita Reyes Ballet Flats
Shop Now
Geri Gingham Maxi Dress
Geri Gingham Maxi Dress
Buy Now
Betabrand Sloane Jean Jacket
Betabrand Sloane Jean Jacket
Buy Now
Bolga Handmade Wicker General Basket
Bolga Handmade Wicker General Basket
Buy Now

 
Cotton On Rib Scoop Neck Long Sleeve Top
 
Converse Chuck Taylor All Star High Top Sneaker
 
Madewell '90s Straight Jean
 
Revolve Harlow Flannel Shacket
Cotton On Rib Scoop Neck Long Sleeve Top
Converse Chuck Taylor All Star High Top Sneaker
Madewell '90s Straight Jean
Revolve Harlow Flannel Shacket
Buy Now
Buy Now
Buy Now
Buy Now
Cotton On Rib Scoop Neck Long Sleeve Top
Cotton On Rib Scoop Neck Long Sleeve Top
Buy Now
Converse Chuck Taylor All Star High Top Sneaker
Converse Chuck Taylor All Star High Top Sneaker
Buy Now
Madewell '90s Straight Jean
Madewell '90s Straight Jean
Buy Now
Revolve Harlow Flannel Shacket
Revolve Harlow Flannel Shacket
Buy Now

How to Take Amazing Apple Orchard Photos

After you nailed down outfits to wear apple picking, you still need a bit of planning to ensure you get the best photos at the orchard as possible. Since I got every fall and always take a ton of photos, I have a lot of tips and tricks up my sleeve. Here are my 3 top tips for having the best photoshoot at an apple orchard! 

Go In The Evening

Have you ever tried taking photos under trees at noon? You’ve probably noticed harsh shadows and bright light blowing out the background.

Not ideal for photos. Plus, in many places, early September is still pretty warm. I can attest from personal experience that apple picking at noon when it’s 90 degrees out is not ideal. 

Instead, head to the orchard in the late afternoon or early evening. If you can get there within an hour from sunset, that would result in amazing photos without harsh light! It’ll be cooler, too. 

Bring Accessories

This is KEY for good photos! Bring a straw bag or a straw picnic basket to style with the apples. You can fill it up with apples and carrying it around to look like a legit cottagecore babe. Bring a plaid blanket, too! You can sit on this or wrap it around your shoulders to really style out the photoshoot. 

Bolga Handmade Wicker General Basket
Bolga Handmade Wicker General Basket
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Get Playful

Take a bite out of an apple. Toss them around a bit, get some movement in there with your photos. Don’t just stand in the middle of the row smiling. You dressed all cute in a fall outfit so really sell the mood! When in doubt, start picking the apples from the tree to take candid photos. They’ll turn out great!

Need an apple orchard Instagram caption? Check out 70+ Fall Instagram Captions SO GENIUS You’ll Want To Use Them All
Revolve Harlow Flannel Shacket
Revolve Harlow Flannel Shacket
Buy Now
ZESICA Flowy A Line Tiered Midi Dress
ZESICA Flowy A Line Tiered Midi Dress
Buy Now
Levi's Women's Vintage Overalls (Also Available in Plus)
Levi's Women's Vintage Overalls (Also Available in Plus)
Buy Now
Hunter Women's Original Short Rain Boots
Hunter Women's Original Short Rain Boots
Buy Now
Aelfric Eden Cable Knit Sweater
Aelfric Eden Cable Knit Sweater
Buy Now
Embracing Autumn Corduroy Pinafore Mini Dress
Embracing Autumn Corduroy Pinafore Mini Dress
Buy Now
Check Pleated Shorts With Belt
Check Pleated Shorts With Belt
Buy Now
Universal Thread Cozy Knit Button-down Cardigan
Universal Thread Cozy Knit Button-down Cardigan
Buy Now
Alice + Olivia Siobhan Vegan Wrap Mini Skirt
Alice + Olivia Siobhan Vegan Wrap Mini Skirt
Buy Now
Presley Plaid Button Down Top
Presley Plaid Button Down Top
Buy Now
Bolga Handmade Wicker General Basket
Bolga Handmade Wicker General Basket
Buy Now
Madewell '90s Straight Jean
Madewell '90s Straight Jean
Buy Now
Geri Gingham Maxi Dress
Geri Gingham Maxi Dress
Buy Now
Betabrand Sloane Jean Jacket
Betabrand Sloane Jean Jacket
Buy Now
Boston Suede Leather Birkenstocks
Boston Suede Leather Birkenstocks
Buy Now
Long Bow Crinkle Scrunchie
Long Bow Crinkle Scrunchie
Buy Now
Dolce Vita Reyes Ballet Flats
Dolce Vita Reyes Ballet Flats
Shop Now
Old Navy Canvas Barn Jacket
Old Navy Canvas Barn Jacket
Buy Now
Logan Over the Knee Boot
Logan Over the Knee Boot
Buy Now
Mini Pencil Skirt
Mini Pencil Skirt
Buy Now
Apple Harvest Sweater
Apple Harvest Sweater
Buy Now
Utility Denim Jumpsuit
Utility Denim Jumpsuit
Buy Now
Cotton On Rib Scoop Neck Long Sleeve Top
Cotton On Rib Scoop Neck Long Sleeve Top
Buy Now
Everlane Luxe Micro-Rib Long-Sleeve Crew
Everlane Luxe Micro-Rib Long-Sleeve Crew
Buy Now
Black Loafers
Black Loafers
Shop Now
Converse Chuck Taylor All Star High Top Sneaker
Converse Chuck Taylor All Star High Top Sneaker
Buy Now
Mini Hoops
Mini Hoops
Shop Now

What to Expect When Apple Picking

The process is really simple actually. After you’ve found an apple farm near you (a simple Google search of “apple far

m near me” should do), there are different rules and forms of payment (i.e. by the basket or by the apple) so read carefully!

Upon arrival, you’ll likely be given a basket or container to collect the apples you’ve picked. Be sure to bring something like a reusable bag or basket to carry your treasures home! 

Next is the fun part! Picking apples. The best way to pick apples is to ask the experts. Those working at the apple farm know it best and can lead you in the right direction!

After you pick your apples, simply pay at the front and head home, or stick around for a picnic. I love hanging out, having a picnic, drinking apple cider and eating apple cider donuts! 

Tips for Apple Picking 

  • Pack the essentials: sunscreen, water bottle, picnic blanket (and snacks!), picnic basket and cooler for drinks
  • Enjoy the view! Sometimes we get so focused on picking apples, we forget to take it all in 😍 Nature’s beauty is something we shouldn’t take advantage of (especially in the fall!)  
  • Avoid bruising your apples after you’ve picked them! Gently place in your bushel or bag. 
  • Use your apples: make something special like a pie or cobbler or simply throw in a salad! 

I hope this helped you plan what to wear apple picking this fall! When in doubt I love to look at Pinterest outfits so if you found this helpful, I would love if you pinned this post to Pinterest so other people can find it!

 
Logan Over the Knee Boot
 
Hunter Women's Original Short Rain Boots
 
Geri Gingham Maxi Dress
 
Betabrand Sloane Jean Jacket
 
Revolve Harlow Flannel Shacket
 
ZESICA Flowy A Line Tiered Midi Dress
 
Levi's Women's Vintage Overalls (Also Available in Plus)
 
Presley Plaid Button Down Top
 
Madewell '90s Straight Jean
Logan Over the Knee Boot
Hunter Women's Original Short Rain Boots
Geri Gingham Maxi Dress
Betabrand Sloane Jean Jacket
Revolve Harlow Flannel Shacket
ZESICA Flowy A Line Tiered Midi Dress
Levi's Women's Vintage Overalls (Also Available in Plus)
Presley Plaid Button Down Top
Madewell '90s Straight Jean
Buy Now
Buy Now
Buy Now
Buy Now
Buy Now
Buy Now
Buy Now
Buy Now
Buy Now
Logan Over the Knee Boot
Logan Over the Knee Boot
Buy Now
Hunter Women's Original Short Rain Boots
Hunter Women's Original Short Rain Boots
Buy Now
Geri Gingham Maxi Dress
Geri Gingham Maxi Dress
Buy Now
Betabrand Sloane Jean Jacket
Betabrand Sloane Jean Jacket
Buy Now
Revolve Harlow Flannel Shacket
Revolve Harlow Flannel Shacket
Buy Now
ZESICA Flowy A Line Tiered Midi Dress
ZESICA Flowy A Line Tiered Midi Dress
Buy Now
Levi's Women's Vintage Overalls (Also Available in Plus)
Levi's Women's Vintage Overalls (Also Available in Plus)
Buy Now
Presley Plaid Button Down Top
Presley Plaid Button Down Top
Buy Now
Madewell '90s Straight Jean
Madewell '90s Straight Jean
Buy Now

Here’s to fall and leaning into our basic fall betch. And making a LOT of apple pies. Soon enough I’ll be writing up holiday gift guides (time flies!)

Kara

I'm the founder of Whimsy Soul (this blog you're reading!) I'm a type 3 enneagram cat lady who lives in San Francisco and loves to find everyday magic to share with others. You can probably find me hunting down hot springs with girlfriends, kayaking, cooking with my husband, petting strangers' dogs or watching like, all the things on Netflix. Follow me on Instagram for even more inspiration!

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