Sip, Style, and Strut: 13 Winery Fall Outfit Ideas for 2023
As the leaves change colors and the air turns crisp, it’s the perfect time to explore cozy winery vibes. But let’s be honest—what’s a wine-tasting adventure without a cute outfit to match? With 2023 in full swing, we’ve rounded up 13 fabulous fall outfit ideas for both women and men that will ensure you look as good as that glass of rosé you’re about to sip. So grab your wine buddy and let’s get stylin’!
Let’s start with the ladies! It’s all about versatility, darling. From flirty dresses to relaxed jeans paired with oversized sweaters, you’ve got options galore. Whether you’re a size 2 or a size 22, there’s a cute outfit waiting to flaunt your style as you stroll through that vineyard. And no need to worry about cold feet—literally! A cute pair of booties can elevate your outfit while keeping those toes warm.
Now, don’t forget about the gents! Men, that oversized T-shirt and gym shorts combo won’t cut it when it’s time for tasting. You deserve to look sharp too! Think flannel shirts layered over a fitted tee and paired with your favorite jeans for a laid-back, yet put-together look. Trust us; your wine glass will thank you for putting in that little extra effort!
What about dress options for everyone? A flowy midi dress for women can be effortlessly chic, and when paired with a denim jacket, you’re ready for any outdoor vineyard experience! For men, a tailored jacket can work wonders—especially when you’re aiming to impress somebody cute while you discuss your favorite cabernet. The right outfit can add that dash of confidence to your day!
Finally, let’s not forget that layering is key this fall! The temperature may drop as the sun sets, but you’re prepared with stylish layers. From funky scarves to cozy cardigans, these accessories not only keep you warm but also add a delightful pop to your ensemble. So, gear up for an unforgettable day of wine and style, because you’ll want to snap those Instagram pics in your winery outfit of the season. Cheers to fashionable fall adventures in 2023!
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#1 Fall’s Wine Fashion Forecast:

This outfit is basically saying “Hey, I’m ready for some wine and some beautiful fall foliage!” That plaid shirt? Classic. Those boots? Made for stomping through vineyards. And that hat? It’s like a little reminder to stay classy even when you’re sipping on that second glass. Plus, the way the leaves are turning makes this pic look like it was taken straight out of a movie. Who needs a fancy dress when you can look this comfy and cool?
You might be wondering, “Why is she walking away?” Well, maybe she’s on her way to meet up with friends for a wine tasting or maybe she’s just about to take in the breathtaking view of the vineyard. Either way, this outfit is giving us all the good vibes for a perfect fall day. Don’t forget to grab a sweater though! It might be a little chilly in the vineyard.
#2 Cabernet Chic:

Imagine you’re strolling through a vineyard, leaves turning golden, the air crisp and cool. You’re on your way to a wine tasting, but you want to look amazing without feeling overdressed. That’s where this outfit comes in! This combo is all about feeling confident and stylish, with a touch of elegance that screams “I know my grapes!” The white top and blush-toned pants are perfect for fall, while the blazer adds a touch of sophistication for those crisp evenings. Plus, those black heels are a classic choice for a reason – they add just the right amount of pizzazz.
With this outfit, you’ll be the talk of the vineyard! You’ll be so cute, people will want to take photos of you with the vines. It’s the perfect balance of comfort and style, which is what every girl wants when she’s sipping on wine and soaking up the autumn atmosphere. So ditch the boring sweaters and jeans, and embrace the fall vibes with this chic, trendy outfit!
#3 Vintage Vibes:

This girl is totally rocking the fall winery look! It’s a classic combination of chic and cozy, with a touch of autumn charm. You gotta love the cute hat and those amazing sunglasses, they’re the perfect accessories for a day spent sipping wine and enjoying the beautiful scenery. The brown jacket is a great way to add warmth and style, and the jeans are the perfect base for a relaxed and comfy outfit. Plus, the wine in her hand just screams “wine o’clock!” You know she’s about to have a great time at the vineyard.
It’s important to remember that even though it looks super stylish, maybe leave the heels at home unless you’re a pro at walking on uneven terrain. Those vines can be tricky! But hey, if you’re feeling confident, go for it! Just make sure to bring a comfy pair of shoes for when you’re ready to kick back and relax with a glass of vino. You’ll be the best dressed person at the winery, and you’ll be comfy too!
#4 Autumn Harvest Fashion:

This picture screams “fall vibes” with its gorgeous autumnal colors and the warm sun lighting up the vineyard. The lady looks absolutely amazing in her casual yet chic outfit: a cute white shirt, a cozy brown jacket, some ripped jeans (who doesn’t love a good pair of ripped jeans!), and some comfy boots. She’s got that perfect “I’m ready for some wine and good company” look. It’s the kind of outfit you’d want to wear to a winery, where you can sip on some delicious wine and enjoy the beautiful fall weather. Plus, she’s holding a glass of wine – making this the ultimate winery fall outfit inspiration!
Remember, it’s all about finding what feels good and confident, no matter if you’re visiting a vineyard or just hanging out with friends. Don’t be afraid to experiment with different styles to find your own unique look! After all, feeling good in your own skin is the best fashion statement.
#5 Wine-Inspired Fashion:

This outfit is perfect for a day trip to the winery! The camel coat is warm and stylish, and the ripped jeans add a touch of cool. The mustard tank top is a fun pop of color, and the heels are just the right amount of glam. You’ll be turning heads all day long!
Remember to grab a glass of wine and soak up the fall vibes with your friends. You’ll be the envy of the vineyard in this outfit!
#6 Grape Escape Fashion:

The woman in the picture looks ready for a day at the winery! Her white blouse and brown pants are the perfect combination for a fall day. She’s got that “I’m about to sip some delicious wine and soak up the autumn air” look going on. With those cool boots, she’s definitely ready to walk through the vineyards and try some delicious wine!
But don’t forget about the cute bag she’s carrying! It’s the perfect size to hold all your wine tasting essentials, like a phone, a small notepad (for writing down which wines you liked best, of course!), and a little something for those inevitable wine-fueled snack attacks. So, if you’re planning a trip to a winery this fall, make sure to take some style inspiration from this picture. You can even find a similar outfit in your own closet – you just have to be creative!
#7 Wine & Wardrobe:

This outfit is perfect for a day trip to a winery! The white lace top and matching skirt are light and airy, making them ideal for warm fall days. The wide-brimmed hat is a must-have for protecting your skin from the sun, and the stylish brown handbag is great for carrying all your essentials – including a bottle of wine to enjoy at home!
Imagine yourself strolling through rows of grapevines, the scent of autumn leaves in the air, a glass of crisp wine in your hand, and you in this gorgeous outfit. You’ll be the talk of the vineyard, and everyone will want to know where you got your amazing style! Just remember, don’t let all the fun and excitement make you forget to take some time to enjoy the beautiful fall scenery!
#8 Vintner’s Vanity:

This girl is ready to sip on some delicious wine and soak in the fall vibes! She’s rocking a stunning burgundy dress that makes her look like she just stepped out of a magazine. The vineyard is a beautiful backdrop with its golden leaves and rows of grapes. I bet she’s headed to a winery tasting!
If you’re ever planning a trip to a vineyard, this is the perfect outfit to steal some style inspiration from. A burgundy dress and some fun jewelry are all you need to look amazing and feel confident while you sip on some delicious wine. Just make sure to pair it with a cozy sweater for when the sun goes down, and you’ll be good to go!
#9 Grapevine Glamour:

This girl is ready for a day of wine tasting and enjoying the beautiful fall colors! She’s rocking a comfy, yet stylish outfit that’s perfect for the crisp autumn air. That long cardigan keeps her warm while still looking super trendy, and the black leather pants add a touch of edge to her look. And let’s not forget about that cute black handbag—she’s definitely got her wine-tasting essentials ready to go!
With that glass of wine in her hand, she’s ready to sip, savor, and soak up all the fall vibes. She’s clearly got a good taste in wine and fashion, and she’s totally killing it with her autumnal style. We’re sure she’s going to have a great time exploring the winery and enjoying all the delicious flavors of the season!
#10 Wine Country Chic:

This outfit is so chic, it could make even the most basic bottle of wine seem fancy! The white coat looks super comfy and stylish, and the black pants and boots are a classic combination that’s perfect for any occasion. This is the kind of outfit you can wear to a wine tasting, a pumpkin patch, or even just to grab coffee with your friends. It’s the perfect blend of casual and cool, and it’s sure to turn heads wherever you go.
This outfit is the perfect example of how to dress for the fall season. It’s warm enough for the cooler weather, but still stylish enough to make you feel confident. And let’s be honest, who doesn’t love a good wine-tasting outfit? This outfit is so versatile that you can easily dress it up or down depending on the occasion. Just add a scarf and some jewelry for a more formal look, or keep it simple with just a cute handbag for a more casual vibe.
#11 Fall Into Fashion: Winery Style

This girl’s got the perfect outfit for a day of wine tasting! With her flowy skirt and cozy cardigan, she’s looking stylish and ready for a good time. Those boots are super cute, but maybe she should save the wine for when she gets to the winery. Who knows, maybe she’s just practicing her “I’m-so-fancy” pose for the gram.
But seriously, this outfit is giving major fall vibes, especially with the beautiful vineyard backdrop. The soft colors and comfy fabrics scream “relax and enjoy a glass of wine.” It’s the perfect blend of chic and casual, and makes you want to grab your friends and hit the road to find the nearest winery!
#12 Fall’s Wine Country Style:

This girl is seriously rocking the fall vibes. Look at those cozy boots! I bet they’re super comfy for walking around a vineyard and trying all the different wines. I love the cute hat, too! It’s the perfect accessory for a day of wine tasting. And don’t forget that amazing sweater – it’s the perfect way to stay warm on a chilly fall day. This outfit is giving me all the autumn vibes, and I am here for it!
I bet she’s about to have a fantastic day at the winery. Maybe she’ll even get a little bit of a wine buzz! And if she does, I’m sure she’ll still be rocking her fabulous outfit. Who knows, maybe she’ll even find a cute guy at the winery to share a glass of wine with! Maybe he’ll be her wine and dine guy, lol! I’m feeling inspired by this picture! I need to go find some comfy boots and a cute sweater. It’s time for me to embrace the fall season!
#13 Fall in Love with Wine & Fashion:

This outfit is the perfect example of how to look stylish and put-together while still staying warm and comfortable. The camel coat is classic and timeless, and it looks amazing with the black turtleneck and boots. Plus, the little black bag adds a touch of sophistication.
Imagine strolling through a vineyard, the leaves turning vibrant shades of red and orange, and the air crisp with the smell of fall. You’d be the picture of effortless style in this outfit, turning heads as you sip on a delicious glass of red wine. It’s the kind of look that screams “I’m here for the good times, but I also know how to dress.”
#14 Sip & Style:

This outfit is ready to impress at any fall winery trip. Imagine strolling through the vineyard, surrounded by changing leaves and the smell of fresh grapes. The long camel coat keeps you warm, while the white boots add a touch of stylish elegance. You’re rocking a comfy, yet polished look that’s perfect for tasting some delicious wine and enjoying the beautiful autumn scenery. You’ll be the best-dressed person at the tasting room, and you’ll be sure to turn heads as you sip on your favorite vintage.
This outfit will make you feel confident and sophisticated, without sacrificing comfort. Who says you can’t look fabulous and enjoy a casual day out? This outfit proves that you can have both! Just add a cozy scarf, a cute hat, and your favorite pair of sunglasses for a complete fall-ready look. Now go get your wine on, in style!
#15 Vine & Vogue:

This picture screams “Fall in love with fashion!” It’s like the girl in the photo is saying, “Hey, I’m ready for some delicious wine and even more delicious scenery.” She’s rocking a chic brown coat that’s perfect for the cooler weather, and her jeans are super comfy, making her look effortlessly stylish. It’s like she’s about to sip on some Cabernet Sauvignon while strolling through the vineyards, and we’re all here for it. We can practically smell the autumn leaves and the sweet grape aromas.
Let’s be real, this picture makes us want to grab a cozy sweater, some comfy boots, and head to a winery ASAP. Who needs a fancy outfit when you can just be you, surrounded by the beauty of fall? Plus, with a glass of wine in hand, who cares if you spill a little on your outfit? It’s all about embracing the cozy vibes, right? We’re definitely stealing her style for our next winery adventure!