Fall truly is my favorite time of year. As the leaves start to change color and the air becomes a bit crisper, it’s the perfect time to gather with friends and indulge in some delicious wine tasting. The wineries, in particular, provide a stunning setting with their beautiful vineyards and rustic charm, and you need the perfect fall winery outfit.

Before you visit a winery, it’s important to consider the dress code. You want to be chic but also comfortable. I’ve rounded up some fall wine-tasting outfit ideas that are both comfy and stylish and will have you sipping your favorite wines in no time. These looks would also be great fall date night outfits. So grab your favorite bottle and let’s go!

What To Wear To A Winery In The Fall

13 Fall Winery Outfits

ruffle dress with knee-high Boots

A ruffle neck swing dress paired with knee-high boots is the perfect choice for your next day at the winery. The flowy silhouette of the dress allows for easy movement while still being chic, and the ruffle neckline adds a touch of femininity. Pair it with knee-high boots for added warmth and a bit of edge. Dress it up with a statement necklace or keep it simple with a scarf and a denim jacket. Either way, you’ll be ready to sip some wine in style.

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white monochromatic look

I love to wear white year-round. With the changing season comes new fashion possibilities, and a white denim skirt paired with a cream cashmere sweater is the perfect start to a fall winery outfit. The skirt is versatile and can be dressed up or down, while the sweater provides warmth and a touch of elegance. And what better way to complete the look than with a pair of white cowboy boots and a chic hat? There are so many great fall hats for women to choose from! You’ll feel stylish and comfortable whether you’re sipping a glass of wine indoors or strolling through the vineyards.

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denim and an oversized wrap

Nothing captures the essence of the season quite like a pair of flare jeans paired with a cozy sweater. Add an oversized wrap for a touch of elegance and warmth, and complete the look with a pair of stylish booties.

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striped sweater dress

As the crisp autumn air settles in around us, it’s the perfect time to pull out our favorite fall fashion staples, like a cozy mock neck sweater dress. This chic and elegant piece is perfect for a day exploring the wine country. Pairing it with a pair of knee-high boots adds just the right touch of sophistication to this classic look.

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dress with a blazer

A black pocket dress paired with a plaid blazer and high heels is the perfect way to enjoy a day of wine tasting. The simplicity of the dress allows the statement blazer to stand out, while the heels will give you a boost of confidence and elegance. So, whether you’re sipping on a glass of red or a crisp white while taking in the picturesque vineyard views, this outfit is sure to make you feel comfortable and stylish all day long.

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sweater and skort

For those who live in areas where the weather is still mild enough to show some leg, a white ruffle smoked blouse and tan skort is a great choice. The ruffles on the blouse add a playful touch, while the skort provides comfort and versatility. To complete the outfit, try pairing it with a pair of knee-high boots which not only look chic but will also keep your feet cozy on those chilly fall days.

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belted dress and booties

An olive green belted utility dress is the perfect choice, offering a touch of sophistication while still being comfortable and practical for a day of wine tasting. Pair it with some chic booties for an added touch of edge, and you’ll be sure to turn heads as you savor the delicious wines and stunning scenery in the cozy autumn atmosphere. When the weather gets cool, throw on a light jacket to stay warm.

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White sweater dress

This gorgeous fall winery outfit is the perfect combination of style and comfort. The soft, warm texture of the sweater dress provides ultimate comfort as you sip on your favorite red at the vineyard. The brown knee-high boots give a trendy yet practical vibe, ensuring you won’t have to sacrifice style for warmth. To complete the look, don’t forget the perfect bag to hold your essentials as you tour the winery.

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ruffle dress with poncho

This ruffled neck dress is a must-have in every woman’s wardrobe this fall. It’s the perfect dress for a day at the winery and can be styled in so many ways. For a cozy fall look, layer it with a poncho sweater and add a belt to cinch at your waist. Not only will this keep you warm, but it will also add some dimension and shape to the dress. This would also look great paired over a midi dress on cooler days. Complete the look with a pair of boots, either ankle or knee-high, and you’re ready to sip wine in style.

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Turtleneck with a Denim skirt

A turtleneck paired with a denim skirt and western booties is the perfect combination of cozy and fashionable. The turtleneck will keep you warm as you sip on your favorite wine, while the denim skirt and western booties add a touch of rustic charm. Finish off the look with a stylish bag and you’ve got the perfect outfit for a day of wine tasting and relaxation. If you love denim as much as I do check out these other jean skirt outfits.

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Plaid pants and a cardigan

Plaid pants have become a must-have item in any fashionista’s wardrobe. When paired with a perfectly flattering bodysuit, it’s a match made in style heaven. For a more polished and put-together look, throw on a cozy cardigan blazer, which is perfect for layering on cool evenings. A day spent at a winery calls for an outfit that’s both fashionable and functional, and there’s no better choice than plaid pants and a classic cardigan blazer.

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Denim and a sweater

There’s nothing quite like a classic pair of denim jeans. The versatility they offer in any wardrobe is unmatched, able to be dressed up or down with ease. Pair them with a cozy boyfriend cardigan and some stylish booties, and you’ve got a simple yet chic outfit that’s perfect for a winery. The boyfriend cardigan offers a relaxed and comfortable fit, while the booties give the outfit a bit of edge. It’s the perfect combination of casual comfort and style, making it a go-to outfit for those days when you want to look effortlessly stylish.

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Black jeans and blazer

When it comes to putting together a chic and effortless outfit, a few key items can go a long way. Black jeans offer a timeless and versatile base, while the white bodysuit adds a touch of sophistication. Top it all off with a boyfriend blazer for an instant dose of polish, and complete the look with a pair of flats for comfort and style all day long. It’s the perfect sophisticated look for a day sipping wine.

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There you have it—13 chic fall winery outfits that are perfect for your next day in wine country. Whether it’s a cozy sweater and jeans or a chic dress with boots, these are all great options. There’s nothing more relaxing than sipping a delicious glass of wine while wearing a beautiful fall look! Whether you go for a romantic, sweet look or something more casual yet chic, make sure that the outfit is practical and comfortable as well as fashionable. Cheers!

Which fall winery outfit is your favorite? Let me know in the comments!