31 Perfect Fall Winery Outfits You’ll Love

This post contains affiliate links and is a member of the Amazon Services LLC Associates Program. If you make a purchase using one of these affiliate or Amazon links, I may receive compensation at no extra cost to you.

What to Wear to a Winery in Fall: 31 Cute Outfits

If you’ve ever found yourself standing in front of your closet before a fall winery trip, staring at your favorite summer dresses and thinking, “What on earth do I wear now?”, you’re not alone. Transitioning your wardrobe from hot summer days to crisp autumn afternoons at a vineyard can feel tricky. You want to be comfortable yet stylish, on-trend without being overly dressed up, and cozy enough for those chilly vineyard breezes. I totally get it.

After researching fall fashion and chatting with friends who frequent wineries this time of year, I’ve pulled together some ideas for fall winery outfits that are equal parts chic and practical. Think layering pieces, comfy boots, and just the right amount of texture and color to feel confident as you sip on a glass of pinot.

Let’s take a look at some seriously cute looks that’ll make getting dressed for your next winery visit a breeze.

What to Wear to a Winery in Fall: 31 Cute Outfits

1. The Cozy Knit and Jeans Combo

This look is perfect if you want to stay cozy while looking effortlessly put together. A chunky knit sweater in a neutral color like cream or camel adds texture to your outfit, while high-waisted jeans provide comfort and a flattering silhouette.

According to Cosmopolitan, “there are many ways to make your summer pieces work for fall with smart layering and intuitive styling.” Throw on some ankle boots, and you’re ready to explore the vineyard without feeling overdressed. The key here is layering—bring along a stylish scarf or a wool hat to add warmth and personality.

2. The Warm Hug Turtleneck Dress

A turtleneck dress is like a warm hug for those cooler fall days. This look is perfect if you’re after something a bit more polished but still super comfortable. Choose a knee-length or midi turtleneck dress in a fall shade like rust, olive, or burgundy.

Pair it with knee-high boots, and you’ve got an outfit that feels effortlessly chic. Add a belt for some extra shape, and don’t forget a crossbody bag to complete the vibe. This outfit keeps you warm but leaves room to play around with accessories like oversized earrings or a floppy hat. Celebrities like Blake Lively have been spotted rocking similar looks during fall outings.

3. The Textured Corduroy Skirt Look

For a touch of texture, a corduroy skirt paired with a crisp button-up shirt is a winning combo. According to Harper’s Bazaar, “corduroy has a timeless allure, more or less like denim, paired with a stylish blazer or an English rib knit sweater.”

Corduroy works beautifully in fall colors like burnt orange or deep brown. A button-up shirt tucked in or tied at the waist gives it a more tailored look, while ankle boots or loafers keep things casual. You could try adding tights if the weather’s on the cooler side for extra warmth and style.

4. The Plaid Blazer Statement

Plaid is a fall staple, and nothing says vineyard chic quite like a tailored plaid blazer. This look works best with a fitted or slightly oversized blazer in earthy tones like green, brown, or navy. Pair it with your go-to skinny jeans and a basic white tee for an effortlessly stylish outfit.

According to Harper’s Bazaar, “the best fall-in-the-city outfits start with your wardrobe essentials: versatile pieces that you can mix, match, and layer.” Ankle boots or loafers can tie the whole thing together perfectly for a day of wine tasting. I’ve seen Taylor Swift pull off similar plaid looks during her casual fall outings.

5. The Chunky Sweater Dress Essential

Sweater dresses are your best friend when it comes to winery trips in the fall. A chunky knit sweater dress keeps you warm, comfortable, and stylish all in one. This look is perfect if you’re in the mood for something a little more laid-back but still fashion-forward.

Choose a dress with some texture, whether it’s cable-knit or ribbed, and pair it with tall boots for a streamlined look. Don’t forget a statement belt to define your waist, and you’re good to go. This outfit also works great if you’re planning on sitting outside and need that extra layer of warmth.

6. The Denim Jacket Layering Trick

When it comes to layering, a denim jacket is a fall essential. This look is perfect for days when the weather’s a bit unpredictable. Throw your denim jacket over a flowy midi dress for a casual yet feminine vibe. Pair this with cowboy boots or ankle booties for an effortlessly cool, country-chic look that works perfectly at wineries.

You could even toss a scarf into the mix if the temperature dips. It’s easy to swap the jacket out for a warmer option if needed, but the denim keeps it laid-back and stylish. Jennifer Aniston has basically made this her signature casual look.

7. The Edgy Faux Leather Leggings

Faux leather leggings are a great way to elevate your fall winery outfit while keeping things comfortable. These leggings have a sleek, polished look that pairs beautifully with a long, chunky cardigan. Add some heeled ankle boots to dress it up a bit, or keep it casual with flats.

This look works because it balances the soft, cozy cardigan with the edgier vibe of the faux leather. Throw on a hat or some layered necklaces to pull everything together. It’s a great choice if you want to look put-together without sacrificing comfort. Fashion influencer Olivia Palermo has been known to rock similar combinations during fall events.

8. The Relaxed Oversized Flannel

This look is perfect if you’re after something relaxed and casual for your winery day. An oversized flannel shirt, either worn open or buttoned up, gives off those classic fall vibes. Pair it with distressed jeans for that lived-in, comfortable feel. Ankle boots or combat boots finish the look and keep things practical for walking around.

If you want to add a little more style, throw on a beanie or a chunky scarf to make it feel more intentional. This outfit is as cozy as it gets while still looking put-together for a vineyard visit. Brands like Madewell and L.L.Bean have great flannel options for this type of look.

9. The Dramatic Knit Poncho

If you’re in the mood for something a bit more dramatic, a knit poncho over black skinny jeans is a winning combo. Ponchos add a layer of warmth and texture without feeling too bulky, making them perfect for winery outings. Pair this look with heeled booties to give it a bit of height, and you’re all set.

You could opt for a neutral-coloured poncho or try something with a bold print to make a statement. Either way, this outfit is relaxed yet stylish enough to wear all day at the vineyard. Style icons like Meghan Markle have embraced the poncho trend during cooler months.

10. The Suede and Silk Contrast

Slip dresses aren’t just for summer! You can easily transition your favorite slip dress into fall by layering it under a suede jacket. The contrast of the silky dress with the textured suede creates a chic and unexpected look.

This outfit works best with ankle boots, and you can throw on a wide-brim hat to give it that fall flair. A suede jacket in a warm tone like tan or rust brings out the season’s colors, while the slip dress keeps the outfit feeling light and feminine for those warmer fall afternoons.

11. The Flattering Wrap Dress

A wrap dress is universally flattering and perfect for winery visits. The adjustable waist means you can customize the fit, and the flowy skirt gives it a romantic vibe. Pair this look with a wool hat in a neutral tone to complete the fall aesthetic. Booties or heeled sandals (if the weather allows) make this outfit feel a little more dressed up, but it’s still comfortable enough for a day of wine tasting.

This look is great if you want to feel effortlessly feminine while exploring the vineyards. Wrap dresses have been a go-to for celebrities like Kate Middleton for their versatility and elegance.

12. The Balanced Cardigan and Skirt

Cardigans and skirts are the perfect fall duo. Choose a chunky cardigan and pair it with a flowy midi skirt to keep things balanced. This look works because it’s equal parts cozy and sophisticated. Ankle boots complete the look, adding a casual yet stylish feel.

You can experiment with textures here by choosing a skirt with a sheen or pattern to add interest. Fashion stylist Emma from Nashville once told me, “The secret to great fall winery style is mixing soft, cozy pieces with something structured—it keeps you comfortable but still polished.” It’s also easy to layer with a scarf or statement jewelry to make the outfit your own.

13. The Sleek Bodysuit and Trousers

If you’re after a sleek, put-together look, pair a fitted bodysuit with high-waisted trousers. This outfit is simple but super chic. The bodysuit creates a seamless silhouette, while the high-waisted trousers add some structure and sophistication. Finish this look with heeled booties or loafers for a polished vibe.

You could try adding a blazer or statement belt to make the outfit feel more complete. This look is perfect if you want something a bit more formal for your winery visit without being overly dressy or uncomfortable.

14. The Luxe Faux Fur Vest

For a luxe fall look, try layering a faux fur vest over a simple turtleneck and jeans. The fur vest adds texture and warmth while keeping the outfit stylish and chic. Choose neutral tones to keep things sophisticated. Pair this with some leather booties, and you’ll be ready for a cozy day at the vineyard.

The faux fur vest adds a touch of glamour to your outfit while still being suitable for a day outdoors. To elevate this look even further, opt for a sleek ponytail and add some statement earrings. Brands like Zara and Anthropologie offer great faux fur vest options.

15. The Textured Sweater and Satin Skirt

This look is perfect if you want to balance cozy and chic. An oversized knit sweater paired with a satin midi skirt creates a gorgeous contrast of textures. The softness of the sweater paired with the sleekness of the satin keeps the outfit interesting and stylish.

You could try a monochromatic look with similar tones for both the sweater and the skirt, or mix things up with complementary colors. Add ankle boots to keep things casual or heeled booties if you want to dress it up a bit more for the occasion.

16. The Luxurious Cashmere Touch

Nothing says fall luxury like a cashmere sweater. Pair it with wide-leg pants for a sophisticated yet relaxed vibe. This look works especially well in neutral tones like beige, grey, or soft brown, which make it easy to accessorize. Wide-leg pants are incredibly comfortable and flow beautifully, adding elegance to your outfit.

You can tuck in the sweater for a more defined waistline or leave it untucked for a looser, laid-back look. Pair loafers or low heels with this effortlessly chic outfit for a perfect day at the winery. If you’re looking for quality cashmere without breaking the bank, Everlane offers beautiful options in classic fall colors.

17. The Flowy Maxi and Denim Pairing

A flowy maxi dress paired with a denim jacket is perfect for a fall day at the winery. The dress adds a touch of femininity and comfort, while the jacket keeps things casual and warm.

According to Marie Claire, “fall color trends include classic autumnal neutrals and electric shades that lend themselves well to fashion,” so choose a maxi dress in a rich fall color like burgundy, olive, or mustard to make it seasonal. For shoes, consider ankle boots or a pair of sneakers for added comfort during your visit.

18. The Classic Camel Coat Elegance

A camel coat is a classic fall piece that instantly elevates any outfit. This look is perfect if you’re looking for something that feels polished yet comfortable. Layer your camel coat over a sweater dress for a cozy yet stylish ensemble. Pair it with knee-high boots for a chic finish, and don’t forget to add some simple accessories, such as a leather cross-body bag or a gold bracelet.

This outfit gives you the warmth you need while keeping everything sleek and elegant. Perfect for those cooler vineyard days when you want sophistication and comfort.

19. The Colorful Printed Scarf Accent

A printed scarf is an easy way to add color and personality to your fall outfit. Whether you’re wearing a basic tee and jeans or a more polished look, such as a blazer and trousers, a printed scarf can tie the entire outfit together.

Choose a scarf with rich autumn colors—think deep reds, browns, or mustard—and drape it over your shoulders or loop it around your neck for a cozy vibe. This look is great for layering, as you can easily remove the scarf if the day warms up during your wine tasting adventure.

20. The Leather and Floral Mix

Florals aren’t just for spring! You can easily transition your favorite floral dress into the fall by adding a leather jacket. The combination of soft, feminine florals with the edginess of leather creates a perfect contrast that’s ideal for winery outings.

Pair this look with ankle boots or even some chunky combat boots if you want to toughen it up a bit, just as Marie Claire wrote: “ankle boots were a standout, offering an avant-garde, edgy alternative to traditional designs”. This outfit totally mixes textures and styles beautifully for a balanced look.

21. The Sleek Ribbed Knit Dress

If you’re looking for something sleek yet cozy, a ribbed knit dress paired with over-the-knee boots is the way to go. The ribbed texture adds interest to the dress, while the over-the-knee boots make the outfit feel more elevated.

This look is perfect if you want to stay warm without sacrificing style. You can layer a long coat or even a trench over the dress for those extra-chilly days. Add a small crossbody bag, and you’re ready to sip some wine while looking effortlessly stylish throughout the afternoon.

22. The Flirty Off-Shoulder Sweater

This outfit combines comfort and a little flirtiness. An off-shoulder sweater paired with velvet pants is perfect for when you want to show a bit of skin but still stay warm. The velvet texture gives the pants a fall-appropriate vibe, and the off-shoulder detail keeps the look interesting.

Add some ankle boots or heeled booties to complete the outfit. You could throw on a long necklace or earrings to add a bit of shine. This look strikes the perfect balance between laid-back and stylish, making it great for a winery visit.

23. The Cozy Oversized Knit and Leather

An oversized knit sweater paired with leather pants is an easy way to look stylish while staying comfortable. The oversized sweater gives off cozy vibes, while the leather pants bring an edgy, polished look to the outfit.

This combination works well for a day at the winery, giving you flexibility in style and comfort. Heeled booties or even sneakers work well depending on the look you’re going for. You can also add a layered necklace or hat to elevate the whole outfit and make it feel more intentional and polished.

24. The Timeless Trench Coat Layer

The trench coat is a timeless piece that instantly elevates any look. Layering a classic trench over a sweater and jeans is a great way to stay warm while looking effortlessly chic. Choose a trench in a neutral tone like beige or camel, and pair it with darker jeans and a cozy knit sweater. Add ankle boots to keep things practical for walking around the vineyard.

This look is all about balance—keeping things casual yet refined. Perfect for those transitional fall days where you want to look put together without too much fuss.

25. The Bold Burgundy Blazer Look

Burgundy is such a rich fall color, and pairing a burgundy blazer with a silk cami and black skinny jeans makes for a stunning winery outfit. The silk cami adds a touch of elegance and shine, while the blazer keeps things structured and polished.

This look is perfect if you want to feel a little more dressed up but still comfortable enough for a relaxed day of wine tasting. Pair this with heeled boots or loafers for an added touch of sophistication. You’ll feel confident, chic, and perfectly suited for fall weather and winery settings.

26. The Flattering Cropped Sweater Balance

A cropped sweater paired with a midi skirt creates a lovely balance of proportions and makes for a flattering silhouette. This look is great for fall because it gives you the warmth of the sweater while still showing off a bit of your waistline.

Midi skirts in patterns like plaid or florals add texture to the outfit, and pairing them with a cropped sweater in a neutral tone keeps it from feeling too busy. Add ankle boots or flats, depending on your preference, and finish the look with some simple accessories for a youthful vibe.

27. The Checked Wool Coat Sophistication

A checked wool coat is a fall essential, and when paired with dark jeans and knee-high boots, it makes for the perfect winery outfit. The coat adds a layer of warmth and style, while the dark jeans keep things casual yet polished. Knee-high boots bring the outfit together, adding both warmth and a bit of height.

You could layer a simple tee or knit sweater underneath the coat, depending on the weather. This look is perfect for those cooler fall days when you want to stay warm but still look stylish and put-together.

28. The Playful Ruffled Blouse Charm

For a more playful and feminine vibe, try pairing a ruffled blouse with corduroy pants. Corduroy is perfect for fall, adding texture and warmth, while the ruffled blouse adds a touch of elegance and softness.

Choose corduroy pants in a rich fall color like mustard, burgundy, or forest green, and pair them with a blouse in a neutral shade like cream or blush. Finish the unexpected look with loafers or ankle boots for versatile styling, as Cosmopolitan puts it: “loafers truly are the ultimate ‘do everything’ shoe for fall and winter.”

29. The Practical Quilted Vest Look

For a more casual and practical winery outfit, try layering a quilted vest over a flannel shirt and pairing it with skinny jeans. This look is cozy, comfortable, and perfect for fall weather. The quilted vest adds an extra layer of warmth without being too bulky.

Choose a flannel in classic fall colors like red, green, or navy, and keep your jeans simple to balance out the patterns. Ankle boots or sneakers complete the look, making it ideal for outdoor vineyard tours or tastings where you’ll be walking around quite a bit.

30. The Chic Longline Cardigan Layer

A longline cardigan layered over a slip dress is a chic yet relaxed way to dress for the winery. The cardigan adds warmth and a cozy vibe, while the slip dress keeps things feminine and elegant. This look works well with ankle boots or even combat boots for a bit of contrast.

Add a statement necklace or earrings to dress it up, or keep it simple with delicate jewelry for a more understated vibe. This outfit is perfect for transitioning from day to evening at the vineyard, offering versatility throughout your visit.

31. The Belted Floral Midi Dress

Floral prints can easily transition into fall when done in darker, richer hues. A floral print midi dress paired with a belt is a flattering and feminine look for a winery visit. The belt helps define your waist, giving the dress a more tailored look.

According to Vogue Scandinavia, “Chelsea boots stand out with their sleek, no-nonsense design and ankle-high cut perfect for autumn,” so pair this with ankle boots or knee-high boots depending on the weather. You can layer a jacket over the dress for added warmth and complete the look with simple accessories.

Featured Products Worth Checking Out

Throughout these outfit ideas, I’ve mentioned some great staple pieces that keep popping up. Brands like Madewell and L.L.Bean have excellent flannel shirts that work perfectly for winery visits. If you’re looking for quality cashmere sweaters without breaking the bank, Everlane offers beautiful options in classic fall colors. And for boots—which are essential for any vineyard outing—Sam Edelman and Frye both make stylish, comfortable ankle boots that’ll take you from grape to glass in style.

Final Thoughts

At the end of the day, dressing for a fall winery visit doesn’t have to be stressful. The key is finding that sweet spot between comfort and style—pieces that make you feel confident while still being practical for walking around vineyards and enjoying the crisp autumn air.

Whether you’re drawn to cozy sweater dresses, edgy leather pants, or classic blazers, there’s an outfit on this list that’ll work for your personal style. Don’t be afraid to mix textures, play with fall colors, and add your own personal touches through accessories.

The best outfit is the one that makes you feel like yourself—just a slightly more polished, autumn-ready version. So grab your favorite boots, layer up, and get ready to enjoy some amazing wine in style. Cheers to fall fashion and vineyard adventures!

DON’T MISS THESE OTHER FALL STYLE IDEAS:

• 23 Beautiful Fall Outfit Ideas for Women Over 50
• 15 Simple Fall Outfits for Everything from Errands to Dates
• The Ultimate Fall Capsule Wardrobe You Need Right Now
• 22 Preppy Fall Outfits That Blend Cozy and Classy