Planning a winery trip this fall? Whether you’re strolling through the vineyard, sipping on a glass of red, or snapping those dreamy golden-hour photos, your outfit should be equal parts chic and comfortable.
Fall winery outfits are all about cozy layers, earthy tones, and a touch of elegance that feels just right for the season. Think sweater dresses with knee-high boots, flowy midi skirts with cardigans, or classic jeans paired with a plaid blazer.
If you’ve been wondering what to wear for wine tasting this autumn, I’ve rounded up 25+ stylish fall winery outfit ideas that’ll have you looking polished yet effortlessly relaxed.
25+ Fall Winery Outfits
1. Elegant Longline Coats & Sleek Monochrome Layers
Spot a chic long beige coat layered over a classic black top and matching skirt, alongside a friend in a striking gray cape and tan boots. It’s all about those luxe layers and monochrome magic for a sunset toast!
2. Chic Layered Knits & Classic Denim
This look pairs a tailored black blazer over a sleek knit top, with relaxed light-wash jeans for that effortlessly cool vibe. Top it off with a crossbody bag and you’ll be ready to stroll the vineyards in style—so easy, so glam!
3. Breezy White Shirt & Vintage Denim
Here, a crisp white shirt is casually draped over a fitted tank, tucked into high-rise blue jeans—perfect for sipping wine as the sun goes down. Add bold blue nails and a wine glass for instant main character energy!
4. Houndstooth Statement Coat & Denim Midi
A timeless houndstooth coat steals the show, thrown over a black turtleneck and a straight-cut denim midi skirt. Finish with tall black boots and a wine glass for the perfect fall winery vibe—so sophisticated, yet totally easygoing!
5. Dramatic Wool Cape & Modern Shorts
This dramatic wool cape in rich grey makes a statement layered over a black top and shorts, with sheer tights and heeled boots for an edgy yet sophisticated winery pick. So chic, you’ll want to twirl in the tasting room!
6. Cozy Charcoal Sweater Dress & Sleek Boots
A luxe charcoal sweater dress gives all the cozy vibes, styled with tall black boots for a polished finish. This look is perfect when you want to feel cute but stay totally comfy for those wine-sipping afternoons!
7. Stylish Black Blouse & Taupe Mini Skirt
A flirty black blouse pairs effortlessly with a taupe mini skirt featuring bold embellishments, and knee-high black boots for that glam fall energy. Ultra stylish for basking in vineyard sunshine and snapping a million cute photos!
8. Leather Moto Jacket & Soft Knit Skirt
A classic black leather moto jacket amps up a simple black top and soft cream knit midi skirt, finished with sleek black boots for a little urban edge with your fall vineyard stroll. Big city vibes, but make it winery!
9. Classic Denim Mini & Rich Brown Trench
Here’s a fab combo—an indigo denim mini dress layered under a chocolate brown trench, styled with detailed brown cowgirl boots. This pairing is the ultimate blend of timeless, rustic, and fashion-forward for a day out wine tasting!
10. Luxe Shearling Layer & Knit Mini Sweater Dress
This look is all about effortless glam with a cream knit mini sweater dress, topped by a luxe shearling jacket draped over the arms. Paired with light suede boots and a statement hat, it’s winery-chic meets cozy cowgirl!
11. Charcoal Off-Shoulder Knit & Washed Denim Midi Skirt
This cozy vibe mixes a chunky charcoal off-shoulder sweater with a washed black denim midi skirt, finished with chic brown boots for an effortlessly stylish, vineyard-ready outfit. It’s relaxed but oh-so-sophisticated!
12. Deep Burgundy Knit Dress & Textured Knee Boots
A slouchy burgundy knit sweater dress steals the show, teamed with tall brown croc boots for a little city-girl polish. This look is refined but still super comfy—perfect for sipping wine on a crisp fall day!
13. Plush Wool Jacket & Sleek Knit Mini
This outfit features a soft gray wool jacket layered over a classic black knit mini dress, paired with elegant brown knee-high boots. It’s a cozy but polished combo—ideal for sipping wine by gorgeous columns!
14. Chic Beige Blazer & Earth-Toned Leather Pants
This ensemble rocks a sleek beige blazer layered over a white top and brown leather pants, finished off with cowboy boots and a wide-brim hat. It’s giving country luxe with a trendy edge for outdoor winery vibes!
15. Denim Jacket & Cream Sweater Dress Layering
A dark wash denim jacket is tossed over a textured cream sweater dress, with tall taupe boots to complete the look. Laid-back, city-ready, and easy to stroll through vineyards or cobbled streets!
16. Classic Black Coat & Fitted Brown Dress
A refined black coat tops a fitted brown mini dress, paired with streamlined chocolate boots for the ultimate cool-girl wine tasting look. Effortless sophistication and fall-ready style in one little outfit!
17. Rich Brown Knit & Leather Mini Set
This chic pairing features a deep brown fitted knit top and glossy chocolate leather mini skirt, matched with tall brown boots and tights. A big brown tote completes this super sleek fall winery vibe!
18. Elegant Neutral Maxi & Relaxed Trench Layer
A creamy knit maxi dress is topped with a light beige trench coat for a look that’s sophisticated and relaxed. Chunky black boots give it a modern edge—perfect for strolling through city streets or vineyards in style!
19. Soft Teddy Coat & Cozy Black Layers
Slip into a fluffy white teddy coat layered over black pieces for instant warmth and major snuggly style. It’s the easiest pick for wine tasting days spent outdoors without sacrificing any cuteness!
20. Timeless Camel Coat & Classic Black Top
A plush camel coat pulls together a black top and crisp white jeans, creating a timeless and preppy look for vineyard visits. Whether sipping or socializing, you’ll look effortlessly put-together with every glass!
21. Sophisticated Gray Blazer & Black Skinny Layers
A classic tailored gray blazer is layered over a black top and sleek black skinny pants for that sophisticated winery vibe. Finished with black boots and a chain-detailed bag, it’s the definition of polished meets modern!
22. Elegant Fur-Trimmed Coat & Sleek Pants
A chic light gray coat with fluffy fur detailing sits over a fitted black top and blue skinny pants, finished with classic knee-high black boots. The look is timeless and just right for wine-tasting by the barrels!
23. Sleek Textured Black Fur & Silver Knit Mini
A soft silver-grey knit mini dress pairs with a black faux fur coat for all the glam warmth, teamed with sheer tights and chunky platform boots. It’s cool-girl edgy but still snuggly enough for a sunset wine moment!
24. Cozy Cocoa Sweater & Asymmetric Denim Midi
An oversized cocoa-brown sweater is tucked into a high-slit, dark-wash denim midi skirt, styled with deep brown knee boots. It’s casual but so stylish—a perfect blend for rooftop wine and fall views!
25. Cropped Suede Jacket & Navy Mini
A chocolate cropped suede jacket is thrown on over a navy mini dress and matched with rich brown knee boots. This combo gives a cool retro feel with a touch of modern edge for sightseeing or sipping wine downtown!
26. Timeless Beige Trench & Black Knit Mini
This outfit pairs a classic beige trench coat over a fitted black turtleneck mini dress, with sheer tights and tall black boots. You’ll look instantly sophisticated—so easy to wear for both city strolls and winery visits!
27. Polished Black Blazer & Satin Maxi Skirt
A sleek black blazer is styled over a chic black satin maxi skirt, finished with elegant beige boots and a straw hat. It’s understated glam, perfect for a sunny day at the vineyard with a glass in hand!
28. Mocha Vest Set & Flowing Maxi Skirt
A mocha brown sleeveless vest and matching top coordinate with a pleated, flowy maxi skirt for a neutral, earthy vibe. Add pointed black boots for that stunning mix of trendy and comfortable at any vineyard!
29. Soft Gray Turtleneck & Forest Green Maxi
This elegant combo features a light gray turtleneck tucked into a flowing forest green maxi skirt with nude heeled sandals for a refined, vineyard-ready look. It’s effortlessly chic and gives major sophisticated autumn vibes for indoor wine tastings!
30. Rich Brown Blazer & Crisp White Denim
A chocolate brown blazer layers perfectly over a cream tank, paired with relaxed white wide-leg denim for that elevated casual vibe. It’s polished but still totally comfortable for wandering the vineyard grounds with a glass in hand!
31. Classic Black Wool Coat & Vintage Blue Jeans
A timeless black wool coat is draped over a black v-neck and vintage-wash straight-leg jeans, finished with tan suede loafers and a structured black bag. This look screams minimalist chic for those cooler winery days!
32. Tonal Beige Knit Sweater & Textured Midi Skirt
A cozy beige sweater pairs beautifully with a matching ribbed midi skirt that has such gorgeous texture and movement. Finished with black pointed flats, this monochromatic look is sophisticated and perfect for golden hour winery moments!
33. Classic Denim Jacket & Cozy Knit
A timeless blue denim jacket is layered over a soft white knit top, paired with black skinny jeans and caramel suede boots. This look is casual, comfy, and so easy for vineyard strolls and crisp fall afternoons!
34. Espresso Blazer & Textured Knit for Fall Layers
A tailored espresso brown blazer layers effortlessly over a chunky brown turtleneck, styled with black skinny pants and tall black boots. This pairing brings out those fall tones—polished but still super comfortable!
35. Luxe Faux Fur & Sleek All-Black Maxi
This outfit brings drama with a plush brown faux fur coat over a chic black turtleneck and ankle-grazing black maxi skirt. Worn with sleek black boots, it’s the ultimate in cozy-glam for wine sipping days among the vines!
36. Plush Fur Vest & Flared Denim
A rich brown faux fur vest cinched at the waist sits over a fitted black top, with classic blue flared jeans and taupe booties. The vibe is retro-posh and oh-so-perfect for a vineyard with stately charm!
37. Rich Leather Midi & Denim Shirtdress
Here we get two stylish takes: one person is serving up cowgirl chic in a sleeveless chocolate leather midi dress and tall black boots, the other choices a denim belted midi shirtdress with western boots. Both outfits are bold and playful, ideal for wine tasting and catching golden hour!
38. Neutral Longline Vest & Camel Blazer with Denim
The first look features a chic cream longline vest over a black top and light blue jeans, while the second rocks a camel blazer layered on a black tee with straight denim. Both are cozy, wine-sipping outfits made for those perfect autumn vineyard hangs!
39. Cropped Cable Sweater & Satin Maxi Skirt
This outfit is all about textures—a cropped cable-knit ivory sweater tops a sleek black satin maxi skirt, finished with classic black boots. It’s elegant, trendy, and gives off that effortless wine country mood!
Final Thoughts
Wrapping up, fall winery outfits are the perfect mix of cozy, classy, and picture-perfect. From chic sweater dresses to casual jeans-and-blazer combos, there are so many ways to look stylish while staying comfortable for a day of wine tasting.
The key is layering—think boots, hats, and soft knits that not only keep you warm but also add that effortless vineyard-chic vibe. So next time you’re planning a trip to the winery, you’ll know exactly what to wear to sip, stroll, and snap those Instagram-worthy photos in style. Cheers to fall fashion and good wine!
