As the autumn leaves crunch beneath our feet and the harvest season begins, it’s the perfect time to hit the wineries and indulge in all that gloriously fermented goodness we love. But hold your glasses! Before you trot off to the vineyard, let’s ensure you’re dressed for the occasion with these fabulous fall outfit ideas for 2023.
Woman or man, it’s essential to find a balance between cute and comfortable. Whether you want to sport a flirty dress or cuddle up in your favorite oversized sweater with jeans, our selection of outfits will cater to all tastes and sizes. Plus, you’ll want to feel fabulous while sipping on that luscious cabernet!
We understand that layering is crucial, especially as temperatures can swing like a pendulum this time of year. So whether you’re planning for a sunny afternoon or a chilly evening, we’ve got you covered with outfit strategies that will take you from day to night seamlessly in style.
The charm of these outfit ideas isn’t just for this year; many will carry beautifully into 2024. Forget about those fleeting trends. Think about timeless pieces that will keep you looking fabulous and wine-worthy for seasons to come!
So settle in with your favorite glass of rosé as we unveil some of the most stylish and comfy winery outfit ideas that’ll make you look and feel like a sparkling gem among the vineyards. Cheers to fashion and great wine!
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#1 Wine & Wanderlust:
This outfit is the perfect mix of stylish and comfy, which is exactly what you need when you’re sipping on some delicious wine. The long coat is a great way to stay warm, and the neutral colors will make you look like you belong in a vineyard. Plus, the classic heels add a touch of sophistication, so you can feel confident even if you’re a little tipsy.
Think of this outfit as your “I’m here for the good wine and good times” look. It’s perfect for a weekend trip to the winery or a cozy night in with a bottle of your favorite red. And who knows, maybe you’ll even inspire your friends to ditch their sweatpants and get their fall fashion game on!
#2 Grape Expectations:
This outfit is perfect for a day trip to the winery! It’s chic and comfy, with a touch of fall flair. The camel coat is a classic choice for cooler weather, and it looks amazing with the black jeans. Plus, the white tee adds a touch of casualness. You’ll be the best-dressed person at the tasting room, and you’ll be ready for any fall festivities.
And let’s be honest, a trip to the winery wouldn’t be complete without a few pumpkins. It’s like a picture-perfect fall scene right out of a magazine! Just imagine yourself sipping on a glass of wine, surrounded by beautiful scenery and wearing this fabulous outfit. You’ll feel like a million bucks!
#3 Fall Winery Glamour:
This picture screams “fall vibes” with the gorgeous autumn leaves and the lady’s stylish outfit. Imagine yourself strolling through a vineyard like this, the air crisp and the sun warm on your face. That tan blazer and those blue pants – they’re seriously chic! But let’s be honest, who can resist a good hat? It’s the perfect way to add a bit of flair to your fall look. Plus, it’ll keep your head warm when you’re sipping that delicious wine!
This whole look is just begging for a cozy afternoon at a winery. Picture yourself surrounded by your friends, enjoying some fine wine and good company. The leaves are changing, the air is crisp, and you’re looking absolutely fabulous! Who needs a pumpkin spice latte when you have an outfit this good?
#4 Wine Country Style:
This outfit is perfect for a day trip to the winery! The camel coat is so cozy and chic, and the boots are perfect for walking around the vineyard. The black turtleneck and skirt are a classic combo that’s always stylish, and the gold necklace adds a touch of sparkle. Plus, who doesn’t love a good pair of thigh-high boots?
Let’s be honest, you won’t just be sipping wine at the winery, you’ll be taking a million selfies! So ditch the boring jeans and grab that stylish camel coat. You’ll be the envy of all your friends, and you’ll be ready for a day of fun and delicious wine. Don’t forget your stylish clutch bag for all those yummy snacks!
#5 Fall Fashionista:
This girl’s got the perfect outfit for a day at the winery! Just look at her – she’s rocking a cozy brown blazer and cute booties that would be totally comfy for a long day of wine tasting. Plus, her white tee and jeans are a classic combo that looks amazing in any setting. Talk about a fashionista who knows how to keep it simple, but chic!
You can tell this gal is ready to enjoy some autumn vibes with her friends. Maybe she’ll even get a little adventurous and try some grapes straight from the vine! Either way, she’s got the perfect outfit for a memorable fall day at the winery – and who knows, maybe she’ll even score some amazing deals on some yummy wines to take home!
#6 Autumn Ambiance:
This outfit is like a glass of wine – it just gets better with time! Imagine strolling through a vineyard in this gorgeous white lace top and matching skirt. The wide-brimmed hat is perfect for keeping the sun out of your eyes, and the cute little purse is just the right size for carrying your essentials. You’ll be the talk of the winery, and all the grapes will be jealous of your style!
Now that you’re ready to go, you might be thinking, “What kind of wine should I get?”. But don’t worry, you can always ask the experts – they’re usually happy to share their knowledge and give you a taste of their best wines. Just make sure you don’t drink too much, or you might end up looking like a grape yourself! After all, you want to remember this fabulous fall outing and all the fun you had!
#7 Wine-derlust:
This picture shows a girl looking totally chic in a winery setting! It’s the perfect fall outfit, with a comfy sweater and boots that will keep you warm while you’re enjoying the beautiful fall colors. The wide-brimmed hat is a great touch, too—it keeps the sun out of your eyes and makes you look super stylish. She looks like she’s about to sip on some delicious wine and take in the gorgeous views.
But honestly, who cares about the wine when you’re looking this good? The leaves are turning, the air is crisp, and you’re wearing a hat that wouldn’t look out of place in a vintage magazine. You could be strolling through the vineyards, or walking around the city, but either way, you’re totally killing the fall fashion game. Just be careful not to step on any grape vines—they can be sneaky!
#8 Autumn Chic:
This outfit is totally giving us “fall vibes,” and it’s perfect for a trip to the winery. Imagine strolling through the vineyards with the crisp autumn air nipping at your nose, your brown coat keeping you cozy, while you sip a delicious glass of wine. Just make sure you don’t spill any on those fabulously ripped jeans! You might need to hold your wine glass with one hand and your cute brown boots with the other so you don’t trip over the fallen leaves.
And let’s be real, everyone loves a good selfie when surrounded by beautiful fall colors, right? This outfit is just screaming for a pic in front of the perfect vineyard backdrop! Just make sure you don’t accidentally get your hair stuck in a vine. (We’ve all been there!) But hey, at least you’ll look great while it happens!
#9 Vines & Vixen:
This outfit is perfect for a day of wine tasting with your friends! The white pants and shirt are super chic and will keep you cool even as you sample all the delicious wines. You can even add a cute scarf or cardigan if it gets a little chilly. The only thing missing is a bottle of wine to take home!
Don’t forget your comfy shoes – you’ll be doing a lot of walking around the vineyard! This outfit is also perfect for a casual date night or a girls’ night out. Just add a pair of statement earrings and you’ll be ready to turn heads.
#10 Fall’s Fashion Forecast:
This outfit screams “wine tasting” and “pumpkin spice lattes” – it’s like the perfect blend of autumnal vibes and fashion-forward flair. The off-the-shoulder lace top adds a touch of elegance, while the wide-legged pants and floppy hat are perfect for strolling through a vineyard. And who could resist that cute little bag for carrying all your wine tasting essentials? Forget the grapes, this is the real “fruit” of fall fashion. This look is so good, it practically makes you crave a glass of Cabernet.
This girl is ready to embrace the fall season in style. With that cute hat and adorable bag, she’s sure to be the talk of the winery. She’s not just sipping wine; she’s living it! And those white pants – they’re like a blank canvas for her to accessorize with all the latest trends. This is the perfect outfit for a day trip to the country or a night out with friends. Whether she’s pairing it with boots or sandals, this look is sure to turn heads. This outfit is the perfect blend of comfort, style, and autumnal charm. Now, where’s the cheese plate?
#11 Autumn’s Wine & Dine:
This outfit is perfect for a day trip to the winery! It’s comfy and cute, with a touch of fall flair. You can’t go wrong with a cozy sweater and a skirt, and the boots are just the right amount of stylish. Don’t forget to grab a hat to protect your head from the sun and keep your hair out of your face while you’re sipping on your favorite vino. Just be sure to watch out for spills, you don’t want to stain your new skirt with grape juice!
You’ll be the envy of all the other wine enthusiasts with this outfit! You’ll be able to stroll through the vineyards with ease and feel confident and stylish while you’re at it. The outfit is perfect for enjoying a glass of wine on the patio and taking some Insta-worthy pictures to remember your day. So, what are you waiting for? Grab your wine, your hat, and your fabulous outfit, and let’s go!
#12 Winery Whispers:
This outfit is perfect for a day trip to a winery. The white sweater is cozy and stylish, and the jeans are a classic choice that can be dressed up or down. The brown boots add a touch of warmth and sophistication. The hat is also a great way to add some personality to your look. And let’s not forget the gorgeous fall foliage! It’s like the winery is giving you a free backdrop for your Instagram pics!
This outfit is perfect for someone who wants to look chic while enjoying a glass (or two) of wine. It’s also great for people who are looking for a comfortable and stylish outfit to wear on a day out in the fall. You’ll be the envy of everyone at the winery! Just remember to take it easy on the wine, and to always be responsible when driving. After all, you want to enjoy your wine and have a safe trip home!
#13 Harvest Hues:
This outfit is perfect for a day trip to the winery! The cozy sweater and long cardigan are comfy enough for a chilly fall day, but the brown pants and heels make you look super stylish, so you can feel confident while you sip on some wine. You’ll be turning heads at the tasting room, and maybe even winning over some grapes!
Plus, the brown and white colors are totally on-trend for fall, and they look great against the background of the vineyards! You could even accessorize with a cute scarf or hat to complete the look. So grab your friends, book a reservation at your favorite winery, and get ready for a fun fall day!
#14 Vintner’s Muse:
The picture shows a stylish lady, rocking a super cute outfit perfect for a winery visit. Just imagine: the crisp fall air, the smell of grapes, and a glass of delicious wine in your hand. This outfit would make you feel like a total autumn queen!
The white jeans and sweater are so comfy, and the brown hat and handbag are adding a chic touch. You could even throw on a cozy scarf for extra warmth. This outfit isn’t too dressy or too casual, just right for enjoying a day of wine tasting and taking some cute pictures with your friends!
#15 Vine & Velvet:
This outfit is perfect for a day of wine tasting and strolling through the vineyards. The white blazer is stylish and chic, but also practical for keeping you warm if the breeze picks up. The brown top adds a touch of autumnal flair, and the white jeans are just the right amount of casual. Don’t forget to accessorize with a cute hat! You’ll be the best-dressed (and most comfortable) person at the winery.
Remember, a little bit of extra warmth for chilly evenings is always a good idea. You’ll be sipping wine and taking in the scenery, so make sure you are comfortable and ready to have a good time. You might even end up looking like a famous wine connoisseur! 😉
