Toast to Style: 10 Fall Winery Outfit Inspirations for Every Occasion
As fall rolls in, it’s time to bundle up against the crisp air and head out for an unforgettable wine tasting experience. Whether it’s an outing with friends or a romantic date, you need outfits that reflect your fun personality while also being comfortable enough to indulge in whatever wine tickles your fancy. Don’t you worry—we’re here to serve up ten fantastic fall outfit ideas that bring together a cute aesthetic with the essential wine tasting casual vibe.
When you think wine tasting, casual yet classy should come to mind. Our list includes a range of outfits, from adorable dresses to trendy wine tasting jeans ready to complement your wine of choice—because, let’s admit, no one looks good with a splatter of zinfandel on their shirt. We’ve carefully crafted ideas that will keep you both stylish and cozy, even as the temperatures dip.
If size has ever been a concern for you when picking outfits, fret not! Our suggestions highlight diverse styles that flatter so everyone can step into the winery with confidence. The focus is on feeling fabulous at any size, allowing you to swirl your glass and share your thoughts on the latest wine trends without a second thought about your ensemble!
Now, if you happen to pick a day where rain is a possibility, we want to ensure you can still rock that ensemble while staying dry. A cute umbrella can become a part of your fashionable look, blending utility with chic style. You’ll be turning heads while dodging raindrops and making your way to that glorious tasting room—trust us, wine never tasted this good!
So, gather your friends, bring out those comfy layers, and let’s toast to fall! With these ten outfit inspirations, you’ll be ready to rule the vineyards and look fabulous doing it, trending into 2024 like the fashion icon you were born to be!
#1 Autumn Ambiance
This girl is looking absolutely fabulous in her fall winery outfit! It’s the perfect blend of cozy and chic, just like the changing leaves outside. You can picture her sipping on some delicious wine while soaking up the crisp autumn air. Those white boots are a perfect way to elevate a simple outfit, and the yellow skirt adds a pop of color that screams “fall”! She’s clearly ready for a day of fun, delicious food, and maybe even a little bit of wine tasting.
Her outfit is basically a lesson in how to dress for fall: layer up with a comfy cardigan, rock a flattering skirt, and add some height with stylish boots. And don’t forget a smile! There’s nothing more inviting than someone who’s excited to enjoy the best of fall. This look is perfect for a day trip to the local winery or just hanging out with friends on a chilly autumn evening. Whatever your plans, you’ll be looking and feeling your best in this effortlessly cool outfit.
#2 Grape Escape
This outfit is perfect for a day of wine tasting at a cozy winery! The stylish white hat adds a touch of class, and the brown boots keep your feet warm while you’re strolling through the vineyards. Imagine yourself sipping on a delicious glass of red wine, wearing this outfit, and surrounded by the vibrant fall foliage. Talk about a picture-perfect day!
The cool weather calls for comfy clothes, and this outfit definitely fits the bill! The white turtleneck and jeans are cozy and cute, and the warm brown coat will keep you snuggled up even on the chilliest fall day. You’ll be the most fashionable person at the winery, and you’ll feel as good as you look. It’s the perfect outfit for a day of fall fun and good times.
#3 Pumpkin Spice & Everything Nice
This outfit is the perfect blend of comfy and classy – just like a cozy night at a winery! The girl in the picture looks like she’s ready for a night of wine tasting and good company, and her outfit screams fall vibes. The white top is super comfy and the leather pants add a touch of edginess. She’s got the perfect look for sipping on a glass of Cabernet Sauvignon while enjoying the crisp autumn air.
Who wouldn’t want to be this girl in this picture? She’s got the whole “fall winery date” thing figured out, from the cute outfit to the confident smile. Her look is so effortless, it’s like she just threw on the first thing she saw and ended up looking like a fashion icon. Maybe she should open a winery and give out fashion tips to her customers! Who knows, maybe she’s already on her way to being the next big thing in the wine and fashion world!
#4 Cozy Crush
This outfit is like a glass of perfectly chilled Chardonnay on a crisp fall day – sophisticated, comfy, and totally ready for a good time. The white jeans and cute boots are like those comfy jeans you wear all weekend, but the blazer and trendy necklace make it feel a little more fancy, like you’re getting ready for a date at the coolest winery in town! The colors are totally fall-inspired, just like the changing leaves outside. It’s a look that says “I’m ready for a good time, but I still want to look stylish,” which is exactly what you need when you’re heading out for a day of wine tasting and delicious snacks.
Just imagine yourself walking through the vineyard, the sun on your face and the smell of grapes in the air. This outfit will have you feeling confident and ready to explore all the different wines and snacks that the winery has to offer. Plus, you’ll look amazing in all the pictures you take with your friends, which is a major bonus! So grab your best friends, put on your favorite fall outfit, and get ready for a day filled with fun and flavor!
#5 Sip & Savor
This outfit is perfect for a day trip to the winery. You’ll be the picture of fall fashion in your ripped jeans and cute cardigan! The wide-brimmed hat will keep you warm in the crisp air, while your white shirt provides the perfect touch of elegance. Just don’t forget to pack a bottle of wine for the ride home, or you might just be wearing this outfit to a hospital after a very long day!
Don’t worry, the jeans aren’t actually ripped – it’s just a cool design. This outfit is all about looking stylish and comfortable while sipping on some delicious wine. Just be careful not to spill any on your cute cardigan!
#6 Wine Not Darling?
This outfit is the perfect blend of comfort and style. The warm brown sweater and jeans give off serious autumn vibes, and the boots add a touch of sophistication. Just imagine sipping a glass of red wine on a crisp fall day while wearing this outfit. It’s basically the definition of a “wine-derful” experience!
Let’s be honest, who wouldn’t want to rock this look while exploring a picturesque vineyard? The beautiful colors of the changing leaves in the background are a bonus! And don’t forget the cute boots, they’re like the cherry on top of a delicious fall pie!
#7 Vine & Vogue
This outfit screams “fall vibes” and “wine time”! It’s like she’s about to step into a cozy winery, sipping on a glass of cabernet while enjoying the crisp fall air. The brown pants and blazer are super trendy, and the white collar adds a touch of sophistication. We love how the outfit pairs perfectly with the warm hues of autumn, and those brown heels? They’re just begging to be worn on a stroll through the vineyard!
Who needs a fancy dress when you can rock an awesome outfit like this? It’s the perfect mix of stylish and comfortable – perfect for a day of wine tasting or a fun night out with friends! Plus, it’s super easy to put together, so you can focus on enjoying the good times instead of worrying about your outfit.
#8 Harvest Chic
These ladies are ready to hit the town in their stylish fall winery outfits. They’ve got the perfect combination of cute and cozy: think warm sweaters, trendy hats, and boots that are ready to stomp some grapes! You can bet they’re all about to enjoy some delicious wine, and maybe even a little dance on the vineyard floor.
Who needs a fancy dress when you can wear a comfy coat and look absolutely fabulous? It’s all about the confidence, right? These ladies are rocking their fall vibes and making a statement that says, “we’re here to have a good time!”
#9 Cabernet Couture
This outfit is giving “fall vibes” with a capital V! It’s like a picture perfect day at a winery, where the air is crisp, the leaves are changing, and the wine is flowing. The floral skirt adds a touch of elegance and whimsy, while the denim jacket keeps things casual and cool. The scarf is the perfect pop of color to add some extra personality. Plus, those brown shoes? They’re literally the definition of “fall fashion goals”.
Imagine you’re walking through the vineyard with your friends, wearing this outfit, and the sun is setting. You’re laughing, taking pictures, and maybe even indulging in a little wine tasting. That’s what this outfit makes you think about – good times with good friends, and enjoying all the beauty that fall has to offer!
#10 Wine Whisperer
This outfit is perfect for a fall day at the winery! The black top and skirt are classic and stylish, and the burgundy shoes add a touch of fall color. You can imagine yourself sipping on some delicious wine, enjoying the crisp air, and looking fabulous while you do it.
Plus, the skirt is so flowy and comfortable, it’s like you’re wearing a cozy blanket. You can imagine twirling around the vineyards and taking some cute pictures for your Instagram. So grab your favorite fall sweater and head to the winery!
#11 Vinyard Vibe
This outfit is like a glass of crisp white wine on a cool autumn day – refreshing and perfect for a day at the winery. The cozy sweater with its orange and white pattern screams fall vibes, while the distressed jeans and sneakers add a touch of casual coolness. You’ll be comfy enough to walk around the vineyard and stylish enough to impress even the most sophisticated wine connoisseur.
Imagine yourself strolling through rows of grapevines, the crisp air filling your lungs. You stop at a cozy tasting room, sip on a delicious wine, and admire the beautiful autumn colors all around. You’re ready for a memorable fall day, thanks to your on-point winery outfit!
#12 Grapes & Grace
These ladies are ready to conquer the fall winery scene, looking effortlessly stylish in their cozy yet chic ensembles. Think comfy sweaters, trendy jeans, and stylish boots — the perfect combo for sipping on delicious vino and soaking in the autumn vibes. They’re ready to chat with friends, maybe even try a few new wines, and definitely snap a few Insta-worthy pics. And hey, who says you can’t rock a cute outfit while indulging in a little wine tasting?
So, ditch the sweatpants and dust off your favorite fall jacket! It’s time to embrace the season with style. These ladies are giving us all the inspiration we need to look and feel our best while enjoying the fall festivities.
#13 Wine Country Glamour
This picture screams “fall winery outfit!” The girl is rocking a super chic black coat and a cute black dress, which is perfect for the crisp fall weather. She’s even got on black tights and boots – seriously stylish! Maybe she’s heading to a winery to sip on some delicious red wine, or maybe she’s just out enjoying the autumn scenery. Either way, she’s looking absolutely amazing! What’s even cooler? Those pumpkins in the background! I mean, can you imagine how cute it would be to take a picture with those pumpkins while wearing this outfit? It’s totally Instagram-worthy!
Okay, so maybe you’re not into taking pictures with pumpkins. That’s cool too! The point is, this outfit is so versatile – you could totally wear it to a school dance, a night out with your friends, or even just a casual day of shopping. It’s all about how you style it! So go ahead, grab your favorite black coat and dress and get ready to rock the fall season in style. You’ll be the envy of all your friends, and maybe even impress that cute guy you’ve been crushing on!
#14 Slay the Sip
This outfit is perfect for a day of wine tasting at your favorite winery! The brown coat and booties are super trendy and cozy, while the white blouse adds a touch of elegance. And let’s be real, the jeans are just the right amount of casual to make sure you’re comfy while you sip and savor all the delicious wines. Plus, the fall colors in the background are the perfect backdrop for your Instagram-worthy winery pics!
You’ll be the envy of all the other wine lovers with this outfit! It’s totally on-trend and totally comfortable, making it the perfect choice for any fall winery trip. And trust me, you’ll be feeling like a total fashionista as you indulge in all those yummy wines. So what are you waiting for? Get out there and enjoy the fall season in style!
#15 Sip & Style
This outfit is like a glass of crisp apple cider on a cool autumn day – refreshing and comfy! The cute sweater is perfect for keeping warm while you stroll through the vineyards, and the ripped jeans add a touch of casual cool. Don’t forget to grab your trusty straw bag for all your wine tasting essentials – because who wants to carry around a heavy purse when you could be holding a delicious glass of wine? This look is totally ready for a day of fun and laughter, soaking up the autumn vibes and trying all the best wines.
Plus, this outfit isn’t just for wine tasting! You can rock it at a pumpkin patch, apple picking, or even just a walk in the park. It’s the perfect blend of fall fashion and comfort, so you can look and feel your best all season long. You’ll be the envy of everyone at the winery in this cute, casual, and totally on-trend outfit.
