What To Wear To The Pumpkin Patch: 15+ Cute & Cozy Outfits

Wondering what to wear to the Pumpkin Patch? We’ve got you covered! See 15+ cute, cozy pumpkin patch outfits and learn the do’s and don’ts of what to wear to a pumpkin patch! 

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Woman wearing black jeans, tan chelsea boots, a white t-shirt and a denim jacket in a pumpkin patch.
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What To Wear To The Pumpkin Patch

A trip to your local pumpkin farm is a quintessential fall festivity—one that we look forward to every year. Perfectly plump pumpkins, hayrides, corn mazes, and apple cider … What’s not to love about this seasonal tradition? Plus, it’s the best time to bust out a cute fall outfit (and maybe get some photos for your IG). 

Ready to get inspired with chic yet comfortable pumpkin picking outfits? We’re sharing exactly what to wear to a pumpkin patch that will have you feeling stylish and subtly on-theme. Whether you’re invested in sweater weather or need some warm-weather options, this style guide is here to help.

Cute Outfits For A Pumpkin Patch Visit

Ahead, you’ll find 15+ chic and cozy outfits perfect for the pumpkin patch, and get tips on what wardrobe choices to avoid! 

Denim midi skirt, sneakers + leather jacket.

@style.your.occasion

get the look:

At the pumpkin patch you definitely want comfortable footwear that you don’t mind getting a little dirty. This look from our Editor-in-chief’s recent visit to @borelharvestfarm is cute and perfect for a September visit. 

Denim midi skirts are very on-trend this season, and paired with a tank and leather jacket, this look is giving fall vibes. 

Pro tip: If you are planning on venturing right into the pumpkin patch to pick pumpkins, swap the denim midi skirt for jeans as pumpkin vines can be quite prickly! 

Leggings, Ugg boots + graphic sweatshirt.

Woman wearing black leggings with a cropped sweatshirt and ugg boots in a pumpkin patch.
@daniellee_esther

This pumpkin patch outfit gives relaxed Sunday morning vibes—and we’re here for it. Who said leggings and a sweatshirt can’t be major outfit inspo?  

Recreate the look with a pair of high-waisted black leggings, leg warmers (yes, they’re back), and a billowy sweatshirt or sweater with a fun graphic. Accessorize with dainty gold jewelry and your favorite sunnies to avoid looking too casual.

Don’t forget shoes! The Classic Ultra Mini Uggs are not only comfy and extremely easy to walk in, but they’re cozy, too. If you haven’t invested in this on-trend fall shoe, this is your sign. 

Striped sweater, mini skirt + combat boots.

Woman wearing a black mini skirt with a black and white striped sweater and black boots outside of a coffee shop.
@doylediary

A striped knit sweater elevates every outfit. We love the oversized look of this one paired with a black A-line mini skirt. 

 The monochromatic black and white is ultra-chic, but the Dr. Martens lace-up boots add a cool, laid-back feel. Make the look better for colder weather by pairing your mini skirt with tights and an oversized denim jacket. 

Remember, if you are going right into the pumpkin patch, bare legs aren’t practical, so keep this fall look for browsing the grounds and enjoying apple cider. 

Cardigan, jeans + fedora hat.

Flat lay graphic of black jeans, black chelsea boots, a cream cardigan, a black hat, gold hoop earrings and a white handbag.
@style.your.occasion

get the look:

The best outfits for the pumpkin patch balance chicness with comfortability, just like the outfit inspo above. 

Start the look with a cardigan opened over a tank top or fully buttoned. Any jeans will work with this outfit, but we love the faded black wash of this straight-leg pair.  

To accessorize, a pair of Chelsea boots and a chic shoulder bag will do the trick. A fedora hat is the cherry on top of an already picture-perfect fall outfit.

Should I wear a dress to a pumpkin patch?

You can absolutely wear a dress to the pumpkin patch grounds or a festival at a pumpkin farm. But, if you are going pumpkin picking right in the pumpkin patch, it’s best to wear pants to avoid the prickly pumpkin vines

If you aren’t going to be pumpkin picking, a sweater dress is always a safe option for a pumpkin patch visit because it’s cozy yet cute. But you could also wear a mini or maxi dress if the weather allows. 

Sweater dress + cowboy boots.

Woman wearing a black sweater dress and red cowboy boots in a pumpkin patch.
@itsnataliecass

Cowboy boots are another on-trend piece that isn’t going away anytime soon. This pumpkin patch look marries a mini sweater dress with cowboy boots for a trendsetting look that feels fun and eclectic.

Any pair of cowboy or knee-high boots will work for this look. But if you have a colorful pair like the one pictured, don’t be afraid to wear them out and make a statement.

Vintage jeans + oversized quilted jacket.

Woman wearing light wash jeans, Birkenstocks, a white t-shirt and a cream coat outside.
@kristenledwards

When heading to the pumpkin patch, you want to wear something cute yet practical. Quilted jackets were everywhere this spring and will be another big outerwear trend heading into fall. 

And, quilted jackets make the perfect transition piece since they can be worn over a tee shirt for a lightweight layer or worn over a thick sweater on cold days.

Trench coat, leather leggings + sneakers.

Flat lay graphic of leather leggings, cream tank top, white sneakers, camel colored trench coat, a black handbag, gold hoop earrings and a white baseball cap.
@style.your.occasion

get the look:

The trench coat – one of the most classic fall layering pieces – is inherently elegant. 

We love that when you pair a sophisticated trench with more casual pieces, like sneakers, a baseball hat, and leather leggings, you get a comfortable yet stylish look perfect for crisp autumn days at the pumpkin patch.

Jacket, mini skirt + loafers.

Woman wearing a black mini skirt with a white sweater and a leather jacket with black loafers in a pumpkin patch.
@labelswithlattes

This look is ideal for a day date at a pumpkin festival, where you want to look cute but not overdressed. The mini skirt and loafers give a preppy aesthetic, while the oversized leather jacket adds a bit of grunge and a much-needed warm layer.

We love the black and white color combo in this pumpkin patch outfit but feel free to play around with other neutrals.

Cargo pants + crop top.

Woman wearing cargo pants and a white tube top with sneakers in a pumpkin patch.
@megan_blair

Cargo pants were hot this spring and summer, and lucky for us, this pant style is still on-trend for fall. Plus, they’re great for wearing to a pumpkin patch.

We love that this look styles a basic cropped top with bold green cargo pants for an unexpected color pop you rarely see once fall begins. And the Converse sneakers are a cool and relaxed addition to the look.

Wear this on a warm September day when the sun is shining and the pumpkin patch is bustling! 

Knit sweater, jeans + quilted jacket.

Flat lay graphic of light wash straight jeans, camel turtle neck sweater, white jacket, navy new balance sneakers, a white handbag and gold hoop earrings.
@style.your.occasion

get the look:

You can never go wrong with a cozy knit sweater or turtleneck to keep you warm on a brisk autumn day. Pair this staple piece with your favorite jeans and a quilted jacket for an elevated, on-trend look.

Rock this pumpkin patch outfit with comfy yet trendy sneakers, like the ever-faithful New Balance 574’s, gold jewelry, and a neutral-colored shoulder bag. 

Oversized cardigan + bootcut jeans.

Woman wearing bootcut jeans, a black t-shirt, a tan cardigan and black boots in a pumpkin patch.
@mercygracehamilton

This is a stylish yet simple look for the girl whose favorite fall accessory is a cozy cardigan. This classic layering piece never goes out of style and is sure to keep you warm as you wander around the farm.

The best thing about a long, oversized cardigan is that you can throw it over any outfit. We love that this one is layered over a black tank top and bootcut jeans. Wearing flared leg jeans lets you show off those cute new ankle boots you just bought and look flattering as you pose for pics in the patch. 

Puffer vest, leggings + combat boots.

Woman wearing black leggings, black boots, a white sweater, a black puffer vest and a white beanie hat in a pumpkin patch.
@ordinarylils

If you’re looking for an outfit that will keep you warm in late October, try this one. The star of this pumpkin patch outfit is the oversized vest that keeps you cozy-warm and is conveniently water and mud-resistant. 

Go with a fuzzy knit sweater, beanie, and leggings. And to finish the look, combat boots and a crossbody bag are practical and provide a cool-girl aesthetic. 

Shacket, jeans + ankle boots.

Flat lay graphic of white jeans, a black sweater, black booties, a black handbag, a green shacket and gold hoop earrings.
@style.your.occasion

get the look:

Still not sure what to wear to the pumpkin patch? Try this effortless fall outfit that’s perfect for pumpkin picking or any other fall activities you have planned. 

A shacket (or shirt jacket) is an upgraded version of the classic button-up shirt or flannel you might commonly reach for in the fall. 

Layer it over tee shirts and bodysuits or wear it with sweaters as the weather gets colder. This look pairs a black sweater, off-white jeans, and black Chelsea boots with a muted green shacket for a pop of fall color. 

Pro tip: If you plan to go right into the pumpkin patch to pick pumpkins, swap the white denim for a darker wash as there’s a good chance you’ll get a bit dirty!

Chunky boots + cropped puffer vest.

Woman wearing light wash jeans, tan boots, a white long sleeve shirt and a brown puffer vest in a pumpkin patch.
@sierrafreeman5

As we mentioned, puffer vests are everywhere this fall, and they just so happen to make the perfect addition to any pumpkin picking outfit. This pumpkin patch outfit idea features a cropped puffer vest that’s cozy, cute, and practical. 

We love that this outfit keeps it simple with a long-sleeve tee and high-waisted jeans, letting the puffer vest do all the talking. Finish the look with practical shoes, like these chunky ankle boots, that will hold up if the ground is muddy.

Cozy sweater + denim jacket.

Woman wearing a cozy sweater and denim jacket with black pants in a pumpkin patch.
@style.your.occasion

get the look:

If there is one fall item everyone should have in their closet, it’s a denim jacket. This casual yet stylish piece is perfect for the outdoors and looks great layered over a sweater like the photo above.  

Play into the casualness of denim by pairing it with black cargo pants and lug sole combat boots. Sunglasses and a crossbody bag keep this pumpkin picking outfit fashionable yet functional.

Varsity jacket + biker shorts.

Woman wearing a black mini skirt, black Doc Maartins, and a bomber jacket in a pumpkin patch.
@solarpowered_blonde

If you’re wanting athletic outfits for the pumpkin patch, this final look has you covered. Biker shorts and a varsity jacket give off an effortlessly cool vibe we can’t get enough of. Bonus: Bike shorts are the perfect comfy alternative to leggings on warm fall days. 

A chunky loafer or statement shoe adds interest to your look. Keep it casual on top by wearing a tee shirt or oversized hoodie.

What colors do you wear to a pumpkin patch? 

When visiting a pumpkin patch, stick to a neutral fall color palette including brown, olive green, maroon, burnt orange, camel, and tan. Other colors like cream, black, and navy are also safe options to wear at a pumpkin patch; just be sure to avoid bright, summery colors like hot pink, coral, or bright blue.

Woman wearing a black leather jacket with a cream sweater and jeans and ugg boots.
@style.your.occasion

get the look:

More Pumpkin Patch Outfit Ideas 

In case you need a little more inspo, here are some more great pumpkin patch outfits to try.  

  • Leather jacket, straight-leg jeans, and Ugg Tasman shoes
  • Oversized bomber, midi dress, and lug boots
  • Cropped sweater, baggy jeans, and sneakers
  • Straight-leg jeans, t-shirt, plaid blazer, and Converse sneakers
  • Leather jacket, leggings, cozy socks, and combat boots

 

We hope you enjoyed these pumpkin patch outfit ideas and have all the inspiration for your next trip!

 

More Style Inspiration You’ll Love:

15+ Ugg Tasman Outfits That Made Us Buy These Cozy Slippers

14+ Chic Plaid Blazer Outfits You’ll Fall For This Season

17+ Modern Fall Winery Outfits For Your Next Trip To The Vineyard

About

Hi! I'm Christal - Editor-in-chief, published author, and minimalist fashion enthusiast! Welcome to Style Your Occasion, your styling inspiration go-to for every occasion, event, party, and trip! Click below to meet the rest of the Style Your Occasion team.

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