Sip in Style: 10 Fall Winery Outfit Ideas for Every Occasion

As the leaves change and the temperature drops, it’s time to get cozy while sipping on some delightful wines. Whether you’re venturing out for a casual wine tasting or stepping it up for a more classy affair, we’ve got your fall winery wardrobe covered. Gone are the days of questioning “What do I wear to wine tasting?” Let’s be honest, showing up in sweatpants may not be the vibe you want to invoke, even if they are super comfy!

Picture this: it’s a rainy day, and you’re braving the drizzle for a day of wine tasting with friends. You want to be both cute and casual while still maintaining that classy flair. Luckily, there are plenty of ways to blend comfort and style that will keep you looking fabulous and feeling cozy. After all, the key to successfully blending in with the vineyard scenery is to wear something that says, “I love wine, and I have great taste!”

For the gents, don’t fret! You can be casual and stylish, too. A great pair of wine tasting jeans paired with a snazzy and somewhat laid-back shirt can keep your look neat without sacrificing comfort. Think of it as looking effortlessly cool while you swirl, sniff, and sip all those lovely wines. After all, when the outfit is on point, it’s just one less thing to worry about while contemplating that vintage Cabernet!

And for those looking for something that hits right in between casual and classy, don’t underestimate the power of a cute dress. Perfect for transitioning as we move into 2024, a fall dress can be beautifully complemented by a cozy cardigan and some ankle boots – just the right combo for that picture-perfect tasting moment. Don’t forget to consider size and fit, because who wants to be uncomfortable when it’s time to make a toast?

So, grab your friends, your itinerary of the best wineries, and get ready to hit the grapevine in style. With our top 10 outfit ideas, you’ll be dressed to impress as you sip your way through the fall. Whether you opt for cozy layers or summer’s last hurrah, just make sure your look is as delightful as that Merlot!

#1 Wine Not? (This one is a classic, and works well!)

This outfit is the perfect blend of comfy and chic, just like a warm glass of apple cider on a crisp autumn day. The plaid dress says, “I’m ready for a good time,” while the brown boots scream, “Let’s go stomp some grapes!” And don’t forget the cute purse – it’s perfect for carrying all your wine tasting essentials, like a little notebook for jotting down your favorite vintages (and maybe even a few “fall selfie” snaps!).

This outfit is not just about looking good, it’s about feeling good, too! Imagine yourself strolling through a vineyard with the leaves changing color all around you. You’re feeling cozy and confident, with a smile as bright as the sunshine peeking through the branches. This outfit is the perfect recipe for a fun and memorable fall winery experience. Now go forth and sip, laugh, and enjoy the season!

#2 Tastings & Threads:

This outfit is perfect for a fall day at the winery! The cozy grey dress looks like it’s made for sipping on some crisp apple cider and enjoying the beautiful fall foliage. And those boots? They’re the perfect combination of comfy and stylish, just like you want to be when you’re out exploring the vineyards with your friends. Plus, that brown purse is perfect for holding all your essentials, like your phone, wallet, and maybe even a little extra bottle of wine to share with someone special.

Remember, it’s important to dress comfortably when you’re heading out to the winery, because you’ll probably be doing a lot of walking and maybe even a little bit of dancing. So put on your favorite fall clothes, grab your best friends, and get ready for a day of fun and laughter!

#3 Vine & Vogue:

This outfit is perfect for a day trip to the local winery! The cozy sweater and jeans are comfy enough for a long drive, and the boots are stylish enough to make you feel like a fashion icon. Who needs fancy dresses when you can rock a comfy but cute look for sipping some delicious wine?

And let’s be real, those ripped jeans are the perfect way to show off your awesome boots! You’ll be the envy of all the other wine drinkers, and maybe even the grape stompers. Just make sure to bring a sweater – those fall evenings can get chilly!

#4 Autumnal Aura:

This outfit screams “fall vibes” and is perfect for a day at the winery! The black dress is super comfy and stylish, and the cute little hat and boots are the perfect accessories. You’ll look amazing sipping on some wine while enjoying the beautiful autumn scenery.

Just make sure to wear comfy shoes because you might be doing a lot of walking! And don’t forget to bring a jacket, because fall weather can be unpredictable. But hey, at least you’ll look fabulous while you’re trying to decide if you want a glass of red or white!

#5 Sunset Sips:

This outfit is perfect for a trip to the winery. The cozy brown sweater and beige blazer are perfect for keeping you warm, while the white jeans and heels add a touch of style. You’ll be looking your best, whether you’re sipping on a glass of Pinot or taking a tour of the vineyards.

Don’t forget to bring a friend! You can even grab a cute photo together with the beautiful fall foliage in the background. And if you’re feeling extra fancy, bring a scarf and some cute earrings to complete the look! Just make sure to steer clear of the grapes. You don’t want to end up with a mouthful of seeds instead of a sip of delicious wine.

#6 Wine & Wonder:

This outfit is the perfect blend of cozy and chic, just like a glass of red wine on a crisp autumn evening. The plaid skirt is a classic fall staple, and it looks amazing with the maroon sweater. The boots are perfect for keeping your feet warm, and the black tights add a touch of elegance. This whole look is screaming “I’m ready for pumpkin spice lattes and apple cider donuts!”

If you’re looking for a cute outfit to wear to a fall winery, look no further! This outfit is comfy enough to wear all day long, but it’s also stylish enough to impress your friends. Plus, it’s super easy to put together. Just grab your favorite plaid skirt and a cozy sweater, throw on some black tights and boots, and you’re good to go! You’ll be the envy of all the other wine lovers.

#7 Vines & Velvet:

This outfit is perfect for a fall winery trip! You can wear it to a tasting or just to enjoy the crisp autumn air. The brown tones of the outfit are super trendy this season and the long boots are perfect for keeping your legs warm. Don’t forget to add some cute accessories like a scarf or a hat! You’ll look absolutely fabulous. Just be careful not to spill any wine on your stylish new outfit!

Even if you don’t own a pair of knee-high boots, you can still get the fall winery look! A cute sweater dress with a chunky belt and some tights will do the trick! You’ll look stylish and feel comfortable while you sip on some delicious wine. And don’t forget to bring a friend! It’s way more fun to go to the winery with someone else. So grab a friend, put on your best fall outfit and go enjoy some wine!

#8 Sip & Stroll:

This outfit screams “Fall vibes” and “I’m ready for a glass (or two) of wine!” That cozy off-the-shoulder sweater looks like it’s perfect for snuggling up next to a fire, but the ripped jeans say “I’m still ready to party.” It’s like the outfit’s saying, “Let’s enjoy the beautiful fall weather and some delicious wine, but I’m not afraid to dance the night away!”

Seriously, this outfit is giving us major “wine country weekend” goals. Just imagine: you’re strolling through a vineyard, the leaves are changing color, and you’re sipping on a delicious Cabernet Sauvignon. Who wouldn’t want to be dressed like this? Plus, the ripped jeans make sure you’re still comfortable enough to do some grape stomping! (Just be careful, those heels are killer!)

#9 Winery Wanderlust:

This picture shows a girl who’s totally ready for a fall day at the winery! She’s rocking a super cute, belted coat that’s totally autumnal and would look perfect with a glass of red wine in hand. And those white boots? They’re the perfect way to add a little something special to her look. She’s clearly ready to enjoy the crisp air, the beautiful scenery, and a delicious tasting of some of the region’s finest wines.

You can’t have a fall winery day without the right outfit, right? This look is all about comfort and style. Imagine strolling through the vineyards, surrounded by the changing colors of the leaves. You’d be the envy of everyone with your cute coat and your effortlessly chic boots! This is definitely a look that says, “I know what’s up,” and it’s perfect for making memories and having a fun time with friends.

#10 Cabernet Chic:

These three stylish ladies are ready to hit the winery in their fall-fabulous outfits! They’ve got the perfect blend of cozy and chic, with hats, boots, and dresses that scream “autumn vibes”. Imagine yourself sipping on some delicious wine while wearing a cute outfit like these, surrounded by the vibrant colors of fall. You’ll be the envy of everyone at the winery with your trendy style and a smile as bright as the autumn leaves!

Who needs pumpkin spice lattes when you can have a glass of wine and a killer outfit? These ladies know how to turn heads at the winery and make a statement. They’re proof that you can be stylish, comfortable, and ready to enjoy the fall season all at once!

#11 Fall Fashion Fiesta:

This outfit is perfect for a day of wine tasting at your favorite winery. The stylish, yet cozy cardigan and jeans will keep you warm, while the white shirt adds a touch of sophistication. The cute hat is a fun accessory that will help you stand out from the crowd. You’ll be turning heads and sipping wine in style!

Imagine you’re walking through rows of grapevines, the crisp fall air brushing against your cheeks, and the warm sunlight shining on your face. You feel a little chilly, so you pull your cardigan tighter. It’s the perfect outfit for a day of wine tasting and exploring the beautiful vineyard. You’re ready to sip, snack, and soak up the autumn vibes.

#12 Cozy Crush:

This outfit is definitely ready for a day at the winery, but I’m not sure if those heels are made for grape stomping! It’s definitely a look that’s sure to turn heads, and it’s perfect for anyone who wants to look and feel their best while enjoying some delicious wine. The green dress is super chic, and the high heels add a touch of elegance. And don’t forget the accessories! A statement necklace and a fancy watch will complete the look.

Now, remember, a winery is a place for fun and relaxation, so don’t forget to bring your sense of humor! After all, what’s more fun than sipping on some delicious wine and laughing with friends? Just make sure you practice your “wine-o-clock” poses so you’re ready for a killer photo op.

#13 Harvest Hues:

This outfit is perfect for a day trip to the winery! It’s stylish but still comfy, so you can sip your wine and soak in the views without feeling like you’re wearing a costume. The brown sweater and pants are super trendy and look great together, and the white sneakers are a fun way to add a little pop of color. Plus, you can totally rock this outfit for a fall picnic or even a day out with friends!

This look is also super easy to put together. You probably already have some similar items in your closet! The trick is all in the layering, so you can mix and match to create your own unique style. The model even took a cute selfie in this outfit, so you know it’s picture-perfect! You can totally capture some great memories with this outfit.

#14 Autumn Ambrosia:

This outfit is the perfect blend of comfy and chic, perfect for a day of wine tasting at your favorite winery. Imagine strolling through the vineyard, surrounded by rows of colorful grapes, with the crisp autumn air nipping at your nose. You’ll be the envy of all the other wine lovers in your comfy jeans and stylish boots, all while staying warm in your cozy brown jacket. It’s the ideal combination for a relaxing day out, without sacrificing any of your personal style.

This look screams “fall vibes,” even without the wine in hand! The brown jacket and boots match the changing leaves, while the white sweater adds a touch of brightness. Plus, those boots will have you feeling like a total fashionista, even if you’re just grabbing a bottle of Pinot Noir. Don’t forget your comfy jeans, because you’re going to be spending a lot of time standing and walking. And hey, who knows? Maybe you’ll even find a new favorite wine.

#15 Grape Expectations:

This outfit is perfect for a day trip to the local winery. The white sweater is cozy and comfortable, and the jeans and boots are stylish and practical. You’ll be able to sip on some delicious wine and enjoy the beautiful fall scenery without worrying about getting cold or uncomfortable. Plus, the brown boots and the colorful leaves will make your Instagram pictures look absolutely amazing. Just don’t forget to take your sunglasses off for the photos, they’re a bit too cool for a casual winery visit!

Imagine walking through a vineyard with the crisp air nipping at your nose, surrounded by vibrant reds, oranges, and yellows. You’re looking great, feeling warm in your sweater, and about to taste some fantastic wine. Now that’s what we call a perfect fall day!