fall winery outfit light jacket black turtleneck black shoulder bag black leather flat tall boots leather mini skirt

10 Fall Winery Outfits: What to Wear to the Vineyard

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My dream fall season afternoon would consist of a little bit of shopping, a little bit of sightseeing, and a final stop at a local winery for a late afternoon snack and drink. Even if wine isn’t your thing, the atmosphere at a winery in the fall is perfect for an afternoon with friends or family, and there’s always the opportunity to grab a soft drink or sparkling water – and maybe even a charcuterie board. While there’s no bad time for a winery visit, fall is my favorite time of year as wineries are often situated in rural areas surrounded by changing leaves and beautiful landscapes. There’s a reason there’s a whole genre of art based around these types of views! And fall winery outfits are a great opportunity to show off your autumn style.

Fall Winery Outfits

If you’re looking for the perfect outfit for a day like this, I’ve put together a list of 10 fall winery outfits that will be perfect for the tasting room, winery tours, or maybe even a bistro seat overlooking the vineyard.

1. leather skirt + turtleneck + light jacket

fall winery outfit light jacket black turtleneck black shoulder bag black leather flat tall boots leather mini skirt

light jacket | boots | skirt | bodysuit | bag | sunglasses

This is the perfect moody fall look for your autumn trip to the vineyard, whether it’s a trip to Napa Valley or a local winery visit. If the weather is just a little bit cool, a light jacket may be all you need! This one in a rich olive green tone is a chic outer layer for wine country casual.

Build your look by starting with a mini skirt, a leather bag, knee high boots, and a turtleneck bodysuit. You can also add tights if it’s cold so you stay warm wandering among the vines (and wines).

2. cream turtleneck + corduroy pants + boots

cream sweater corduroy khaki pants brown sweater ankle boots sunglasses

turtleneck | pants | sunglasses | boots

Ankle boots with a small heel are chic but comfortable shoes for your fall winery outfits. Or, if you want to go with a pair of even more comfortable shoes, a pair of sneakers would also look great with this look as well. But going back to boots, a rich chocolate brown pair is the perfect choice for a classic cream outfit like this one.

Choose a cozy cream turtleneck for a versatile and neutral top, then add in a different texture with khaki corduroy pants for visual interest. Add sunglasses in your personal style for your wine tasting attire, and you’re ready to have the best time on a wine tour.

3. midi dress + denim jacket + straw tote

lady jacket denim polka dot midi dress flats woven tote bag

jean lady jacket | midi dress | bag | shoes

Black and white polka dots are one of those vintage-inspired patterns that remind me of Audrey Hepburn and classically chic stars. For a look reminiscent of a day spent in Tuscany, a denim jacket in the lady jacket style is an elegant layer without making midi dresses like this one too formal.

Add a basket bag to further the feel of lounging at a winery in the Italian countryside. Plus, there’s plenty of room inside for a bottle of wine (or two) if you take one to go! This bag also doubles as a great idea for a picnic basket. Finish the look with a pair of comfortable shoes like this pair of flats with an ankle strap for added support. This look is the perfect balance of playful and chic.

4. silk dress + woven bag + cowboy boots

midi dress dark green woven pattern shoulder tote bag white cowgirl boots sunglasses

midi dress | boots | bag | sunglasses

There’s something about dark green in silk or velvet that will always feel like fall to me. Midi dresses in moody green are a great choice if you’d like an elevated look for your fall winery visit. The cinched knot in the middle of this one offers a flattering silhouette that will cinch in your waist, and draw slimming attention toward your midsection. Plus, there’s something so romantic about flowy dresses and wineries!

Now, let’s talk about the Western trend. Whether you’re in Paris or the United States, Western-inspired attire and footwear are currently trending. If you’re not quite sure how to adapt the trend to your personal style and taste, try a more subtle take – like these ankle boots. They have just enough Western detail to give you the vibe of cowboy boots, but you don’t have to fully commit to fringe and a hat. This way, pieces like these boots can become a part of your staple wardrobe too, and not just a purchase to satisfy a temporary trend.

Next, this bag is perfect for a fall winery to hold everything you need for an afternoon at the vineyard, plus the rich, dark leather is great for fall. The basketweave pattern is beautiful and is an eye-catching element that makes it unique.

Complete the look with a pair of sunglasses. A classic black pair like these frames would be perfect to finish out the sophisticated, timeless look.

5. wrap dress + loafers + wool socks

fall winery outfit wrap dress velvet shoulder bag loafers high socks

wrap dress | bag | loafers | socks

In place of your typical summer sundress, adapt the warm weather staple for fall by choosing a wrap dress in an autumnal floral pattern – like this black and white one. Depending on your personal style (and your local weather!) you could choose a version in a mini, midi, or maxi dress. Add a bit of drama with unique details on the dress. This one has a great puffed sleeve that adds a fun look to your fall winery outfits.

Need to warm up the look? Adapt the look even further for fall at the winery with your accessories. Warm up the look (literally!) with thick wool socks, a pair of leather loafers, and a velvet bag in a rich fall tone. This one in chocolate brown would be a great choice. If you’re cold, you can always switch out the socks for tights, choose the dress in a long-sleeved version, or add a cozy sweater or blazer on top to complete the chic look.

6. striped sweater + jeans + leather bag

fall winery outfit striped sweater sunglasses leather tote bag loafers

striped sweater | jeans | bag | loafers | sunglasses

There’s nothing I love more in the fall than a classic striped pullover sweater. It’s effortless, timeless, and easy to dress up or down to fit the occasion wherever you’re headed. In the case of a wine tasting at your local vineyard, a pair of jeans is the perfect choice.

When it comes to choosing your jean style, let me ask you a question. Do you already have a go-to comfort style of a nice pair of jeans? Maybe you always go for skinny jeans or a slim fit. This is a great time to try going outside of your comfort zone with a new style. If you usually choose a tighter fit, this sweater is the perfect piece to try pairing with a flared or wide-legged style. Leather loafers will work well with almost any jean style, so they’re the perfect shoe to choose for this look.

To complete the outfit, add a leather bag and sunglasses for a glass of wine at the local winery.

7. striped cardigan + pleated shorts + ballet flats

fall winery outfit striped cardigan shorts flats woven bag

striped cardigan | woven bag | ballet flats | chino shorts

The lady jacket is everywhere this season, and with good reason, It’s a classic wardrobe staple that always looks elegant. And it looks chic no matter how old you are or what you wear it with – even shorts!

This cardigan is a slightly different take on the lady jacket, and is less structured than the typical style. If you’re planning on strolling the vineyards, this may be a bit more comfortable for your fall winery outfits! Do you want even more ease of movement? If it’s not too cool where you live, try pairing the sweater with elevated shorts like these pleated chinos. And when the weather is cool, you can’t go wrong with a pair of jeans or trousers.

To add a more casual element to the chic outfit, I love the idea of adding a basket-style bag. It makes the whole look feel very French-inspired. Add comfortable but always chic flats to finish out the look, and you’re ready to start wine tasting.

Looking for more ways to balance elegant and casual pieces? There’s a guide for you as part of the free resource library. You can sign up for it here.

8. cream turtleneck + camel coat + flared jeans

fall winery outfit camel cardigan coat cream turtleneck flared jeans ankle boots sunglasses

cardigan coat | flared jeans | turtleneck | sunglasses | boots

There’s nothing that gets me more excited for this time of year than breaking out my cozy turtlenecks and favorite overcoat. Plus, this outfit practically screams “winery visit dress code” for fall!

A classic striped or solid turtleneck will always be a chic starter piece for wine tasting outfits. Neutrals especially always look sophisticated and put together. Next, you can’t go wrong with a well-fitting, quality pair of jeans. A flared style like this is perfect for fall because you can wear it with almost any shoe! Whether it’s high heels, loafers, flats, or boots, flared jeans are a great option.

This pair of ankle boots offers you a little height with block heels, while still being comfortable. Maybe you’re walking to the next wine shop or winery hopping in Napa Valley! For an updated version of the ankle boot trend, the square or pointed toe is generally more flattering.

Next, add a coat according to your personal style. I love the camel look, which never goes out of style. Plus, the light brown tone looks great with the cream turtleneck, for a seamless and almost monochromatic pairing. These two will always make you look put together!

9. short-sleeved turtleneck + gold earrings + leather pants

fall winery outfit leather pants short sleeve turtleneck shoulder velvet bag mule heels gold earrings

short sleeved turtleneck | leather pants | mule heels | gold earrings | shoulder bag

If the weather is still too warm to wrap up in a cozy sweater, a short-sleeved turtleneck in a thinner knit like this is a great choice instead. One with a thin vertical ribbed pattern like this is especially slimming, and elongates your torso by drawing the eye either up or down.

As for pants, I love the look of leather in camel for something different! If you’re wanting to try the look in a different way, I love the flared look of this pair. Plus, leather is a great material for fall, as it’s often too warm to wear in the summer.

Finish the look with a pair of clog mules, and a navy blue velvet purse. Add gold statement earrings for a classic, chic look for the winery.

10. button dress + cowboy boots + denim jacket

fall winery outfit button dress jean denim jacket shoulder bag cowboy ankle boots gold earrings
fall winery outfit button dress jean denim jacket shoulder bag cowboy ankle boots gold earrings

dress | saddle bag | white cowboy boots | jean jacket | gold hoops

Are you on the hunt for something with a bit of color to pair with your glass of wine and fall winery outfits? A dress like this one has a classic silhouette, with great detail in the top to bottom buttons. Plus, it’s nice and cool if you’re sitting in the sun for an afternoon lounging and socializing. This could easily be swapped out for a maxi dress as well, if you prefer a longer length.

If the sun sets and the temperature starts to drop, throw on a denim jacket in a light wash for an added layer. If you want to play with the Western trend, these boots are the perfect addition to the winery look. Gold earrings and a leather saddle bag complete the look with classic details.

What’s Next?

Now that you have a list of 10 fall winery outfit ideas to choose from, you’re all set for a great afternoon at the winery. Plus, you can mix and match pieces from these classic pairings to fit your personal style, and with pieces that you might already have. A day with friends and a wine glass in hand is the perfect time to try out fun and new chic looks!

Afterward, are you heading out for dinner? If you’re looking for more classic and chic fall outfits to wear for dinner, you don’t have to go very far. 10 Classic and Trendy Dinner Outfits for Fall.


Hi, I'm Cassie! My husband and I have a full house with three furbabies, and when I'm not spending time with them, I'm loving all things fashion, travel, and romanticizing life's little moments. I'm also a self-described book nerd, and am always on the hunt for my newest read.