There’s nothing quite like an apple picking adventure on a crisp, autumn day.
Wandering through rows of trees filled with vibrant red, yellow and green apples, the sweet scent of fruit filling the air.
It’s a quintessential fall activity that’s fun for all ages.
When heading out to the orchard, you’ll want to dress stylishly for the occasion.
The right outfit will keep you comfortable while looking fashionable as you stroll, select apples and pose for photos.
I’ll also share some of my own tips and experiences accessorizing and wearing these stylish ensembles on my trips to the apple orchard over the years.
So grab your basket and let’s go pick some apples!
Casual Plaid Button-Up
Plaid is a pattern that never goes out of style for fall.
For the orchard, opt for a casual plaid button-up shirt in autumnal colors like rust, olive green and burnt orange.
\ Look for one made from a soft flannel material, which will keep you cozy on chilly days.
Pair your plaid top with stretchy skinny jeans in a dark wash.
\Black or gray jeans work nicely for an outfit with a lot of pattern.
Slip on lace-up ankle booties or low-heeled ankle boots in brown leather or suede.
This adds another texture to the look.
Accessories can really pull this outfit together.
Drape on an oversized blanket scarf in a solid color like cream or light gray.
Add a brown crossbody bag, like one made of soft leather or canvas.
For an extra autumn vibe, wear a knitted beanie in a color that coordinates with the rest of your look.
I love this plaid button-up outfit because it’s so versatile.
Just by changing up your accessories and footwear, you can modify the look.
I’ve worn it apple picking with both booties and sneakers.
A crossbody bag is handy for carrying apples or anything else you purchase, freeing up both hands for the important job of apple selection!
Sweater Weather
Bundling up in cozy sweaters is one of the best parts of fall.
For the orchard, choose an oversized sweater in a fall hue like mustard yellow, forest green or burgundy.
Pair it with cropped, cuffed jeans or leggings and ankle boots.
Look for a sweater made from a warm material like wool or alpaca.
I have an oversized yellow cable knit one that’s perfect for apple picking.
The wool helps keep me warm but isn’t too hot for walking around the orchard.
Cropped jeans are a stylish choice, showing off a peek of ankle that coordinates with your boots.
Or wear solid colored leggings for maximum comfort while squatting to grab apples.
I prefer a darker wash jean or black leggings with my bright sweaters.
Complete the look with ankle boots or booties.
Consider a block heel or lug sole for traipsing over uneven ground.
I like to wear my go-to black suede booties with this outfit.
Don’t forget your beanie or other warm accessories like gloves or a circle scarf.
This sweater outfit is one of my favorites because it’s cute but also practical.
The oversized knit with leggings or jeans provides warmth and coverage while still looking stylish.
I stay cozy all day long picking apples in an ensemble like this.
Trendy Overalls
Overalls are back in style and what better place to wear them than the apple orchard!
Opt for overall shorts or pants in a light wash denim or even a fall color like mustard yellow.
Pair them with a long sleeve t-shirt or mock neck top and sneakers or booties.
Look for overalls with an adjustable strap at the shoulders so you can customize the fit.
The mock neck adds a touch of modern style and pairs nicely with the vintage vibe of overalls.
In cooler weather, wear them over a turtleneck.
On bottom, go for a white or black t-shirt or long sleeve tee.
Tuck it in neatly to show off the overall silhouette.
I prefer high-top converses or ankle boots to complement the casual cool look.
Accessories like a beanie, backpack purse and oversized sunnies add extra flair.
I love wearing my mirrored aviator sunglasses and a black backpack with this outfit.
The backpack is great for holding all the apples and accessories.
This trendy overalls outfit is comfortable, movable and super stylish.
I’ve worn it both in summer with sandals and in fall with boots.
It’s one of my favorite go-to looks for wandering the orchard rows and filling my basket.
Fall Layers
Apple picking comes with unpredictable weather, so embrace fall’s layering trend.
Start with a tank top, long sleeve tee or turtleneck base.
Over that, add an open flannel button-down or shacket.
Finish with a denim or leather jacket.
For the base layer, go for a fitted tank, tee or turtleneck in black, white or autumnal colors.
This anchors the outfit beneath all the layers.
Over that, layer on an open flannel shirt or shacket in plaid, buffalo check or solid color.
Top it off with a classic denim jacket in blue, black or white.
Or for a slightly dressier option, choose a moto-style leather jacket in black or brown.
This pulls the look together while adding warmth.
On bottom, pair this with jeans, leggings or corduroys along with ankle booties, riding boots or chunky sneakers.
Accessorize with a circle scarf or use the flannel shirt as an accessory by tying it around your waist or shoulders.
I love this layered look because you can mix and match pieces.
I’ll often wear the same tank, flannel and denim jacket but switch up my shoes and accessories.
Layering keeps me warm but I can peel pieces off if I get too hot while wandering the orchard.
Romantic Maxi Dress
For a more feminine vibe, wear a romantic maxi dress or skirt.
Opt for one in fall hues or pretty prints like floral, paisley or gingham.
Pair it with boots or booties and add a denim or leather jacket on top.
Look for a maxi made from a soft, flowy material like chiffon, crepe or jersey.
A midi dress or skirt also works well.
I love floral prints and earthy solid colors like rust, olive green and blush pink.
Pair your dress or skirt with ankle boots, either flat or heeled.
I like to wear a denim jacket over top to offset the feminine vibe.
A moto jacket also looks cool with the floral patterns.
Bring along a large tote bag or backpack to carry your apple picking gear in style.
Accessorize with boot socks or tights and dainty jewelry like layered necklaces or hoop earrings.
Finish with a scarf or headband for your hair.
I really enjoy wearing long flowing skirts and dresses apple picking.
They’re so twirly and fun to walk around in.
But the ankle boots and jacket keep the outfit grounded.
My floral maxi with a denim jacket is one of my favorite looks.
Athleisure Wear
For ultimate comfort, go for an athleisure wear outfit.
This look pairs athletic staples like leggings, sneakers and hoodies with casual pieces you can also wear every day.
It’s stylish but designed for ease of movement.
Start with black leggings or yoga pants, which allow you to squat, stretch and move freely while apple picking.
Add an oversized hoodie, zip-up jacket or flannel top.
Finish with chunky sneakers.
I love wearing full-length or cropped leggings paired with a hoodie in charcoal, blush or olive green.
A baseball cap and sunglasses give off sporty vibes.
Switch your sneakers for booties or ankle boots for a bit more polish.
This athleisure look transitions perfectly for running errands after the orchard.
Simply swap the hoodie for a denim jacket and you have a casual weekend outfit.
I appreciate the movement and machine washable practicality of my leggings and sneakers.
Western Inspired
Channel farmhouse chic with a western inspired outfit.
Start with cut-off denim shorts or a denim skirt.
Pair it with a plaid button-up tied at the waist or one of this season’s trendy prairie dresses.
Look for shorts or a skirt in classic blue denim or black.
A midi or maxi length prairie dress also has a great western vibe.
For a top, plaid, gingham and pinstripe button-downs work well.
Knot the front for a DIY crop top effect.
On bottom, wear cowboy boots or booties to complete the look.
Fold the sleeves of your button-down and add accessories like a cowboy hat, bandana or bolo tie.
I love incorporating western details like boot socks or a fringed suede purse.
This western outfit is fun and comfortable for apple picking adventures.
Denim skirts allow easy movement while prairie dresses look super cute but don’t restrict your range of motion.
Cowboy boots also work well on uneven orchard grounds.
Yee-haw!
Neutrals & Earth Tones
You can never go wrong wearing neutrals and earth tones for fall.
Create an effortlessly chic apple picking outfit by pairing pieces in different shades of white, black, gray, tan and brown.
Start with skinny jeans, leggings or trousers in black, gray or white.
Over top, wear an oversized sweater or pullover in ecru, tan, chocolate brown or heathered black.
Finish with booties, ankle boots or brogues in black or brown leather.
Look for cozy knit sweaters with fun details like side slits, mock necks or bell sleeves to elevate your neutral outfit.
Accessorize with a blanket scarf or crossbody bag in cognac, ivory or olive.
A wide-brim hat like a floppy felt one adds a refined touch.
I love wearing neutral layers like a white turtleneck tucked into tan trousers with black booties.
It’s endlessly versatile for crisp fall days.
A creamy chunky sweater paired with gray jeans also creates a minimalist, stylish look perfect for wandering the orchard.
Bold Colors
Bright, bold colors instantly liven up any fall outfit.
For apple picking, pair eye-catching hues like red, purple and teal together for a fun, fashionable look.
Make a statement up top with a colorful cropped sweater or wrap top.
For pants, go for a dark wash jean, black leggings or leather trousers.
Finish with ankle booties in a coordinating or contrasting color.
Look for knit tops in festive autumn shades like pumpkin orange, mustard yellow, cherry red and emerald green.
A skinny scarf or bold, beaded necklace can pull the look together.
On bottom, black is a slimming choice that lets your colorful top pop.
For footwear, pick a color that either matches or purposefully contrasts with your top.
I’ll often pair red booties with a purple sweater or green ones with an orange top.
This unexpected color combo looks so lively on an autumn apple picking adventure.
Don’t be afraid to experiment with bold colors and patterns together.
Plaids, florals and color blocking create eye-catching outfits suited for the activity and season.
It’s fun to stand out in the orchard rows in vibrant hues!
Feminine Dress & Sneakers
An easy way to look stylish for apple picking is pairing a feminine dress with casual sneakers.
The unexpected combo is both cute and practical.
Opt for a flowing minidress, fit and flare midi or A-line maxi in autumnal prints.
Florals, gingham and paisley prints with rich reds, oranges and yellows have a boho vibe perfect for the orchard excursion.
Ground the floaty dress silhouette with chunky sneakers.
White or black sneakers work with any color scheme.
Or go bold with bright colored ones in shades like red, sky blue or mustard yellow.
For extras, layer on a denim jacket or drape a blanket scarf around your shoulders.
Hoop earrings, dainty necklaces and a satchel bag add polish.
Top it off with a felt wide-brim hat for an eclectic, stylish look.
I adore wearing floral dresses with my white sneakers when apple picking.
The sneakers allow me to comfortably walk around all day while the dress keeps the outfit feminine.
It transitions well for day or night activities too.
Preppy Vibes
Channel fall fashion from a bygone era with a preppy outfit combo.
Pieces like wool skirts, cable knits, collared blouses and loafers exude retro vibes perfect for perusing the orchard.
Start with a collared blouse or tie-neck top in a jewel tone like emerald, sapphire or amethyst.
Tuck it into an A-line mini or midi skirt in a tweed or houndstooth pattern.
Finish with low-heeled ankle boots or penny loafers.
Look for posh but practical pieces like wool circle skirts, mock neck blouses and knit twinsets.
A Peter Pan collared top adds playful prep style.
Complete the outfit with textured tights and a crossbody bag with a shoulder strap.
A coordinating plaid blazer or knit cardigan gives you an extra layer for changing temperatures.
This preppy outfit lets you channel studious fall fashion while feeling comfortable navigating the orchard terrain.
Leather Weather
When picking apples on cold crisp days, nothing keeps you warmer than leather.
Construct the ultimate apple picking outfit with key leather essentials.
Start by layering a mock or turtleneck bodysuit underneath buttery soft leather or faux leather leggings.
Add an oversized sweater or flannel on top.
Finish with a moto jacket and ankle boots or booties.
Stick to black or brown leather pieces for a sophisticated monochromatic look.
Or branch out with colored variations like olive green motorcycle jackets and caramel toned shoes.
Leather gloves and a beanie protect your fingers and head from frosty temps.
Carry a large leather tote filled with picnic supplies and apples you pick.
A mini backpack shaped like an apple is an absolutely adorable option!
I love wearing my leather leggings and moto jacket paired with a cream sweater to the orchard.
It’s comfortable, stylish and keeps me so warm while picking apples on brisk autumn days.
I feel invincible wandering the rows in my leather pieces!
Relaxed Boyfriend Jeans
A relaxed denim-on-denim outfit is the perfect unfussy apple picking look.
Pair baggy boyfriend jeans with a casual tee or sweatshirt and sneakers.
Add layers like flannels or jean jackets as desired.
Look for loose fitting boyfriend jeans with a comfortable mid or high rise waist.
Cuff them slightly for a casual, laidback vibe.
On top, wear them with an oversized graphic tee, solid color sweatshirt or neutral bodysuit.
Ground the look with classic white sneakers like Converse Chuck Taylors or Vans.
I’ll often bring a pair of comfy Slip-on Vans along to change into after a long day walking around the orchard.
A flannel tied around your waist camouflages any unwanted bulges from too many apple cider donuts!
A baseball cap and sunglasses add sporty flair.
This relaxed outfit allows you to focus on apple picking rather than your clothes.
With so many chic style options, you’re sure to look amazing on your next apple picking adventure.
Just don’t forget to accessorize with scarves, hats and boots suited for the orchard terrain.
Use these apple picking outfit ideas as inspiration to start planning what you’ll wear on your upcoming trip.
Keep comfort and functionality in mind as you wander through rows of trees and tote baskets brimming with fresh apples.
But most importantly, have fun and savor the beauty of autumn during this quintessential fall activity looking your stylish best.
