Thereās just something magical about a winter winery visitāthe cozy atmosphere, the rolling vineyards wrapped in chillier air, and of course, a glass of red wine in hand. But figuring out what to wear? Thatās where it gets tricky. You want to look stylish and put-together without freezing or feeling overdressed.
These 25+ winter winery outfits are all about striking that perfect balance between warmth and elegance, with cozy layers, chic textures, and effortless pieces that feel right at home among the vines.
Whether youāre planning a weekend wine tasting or a romantic winter date, these outfit ideas will have you looking polished, comfortable, and totally winery-ready.
25+ Winter Winery Outfits
1. Sleek Black Suit and Satin Layers
Sheās rocking a chic black tailored blazer over a matching black top and wide-leg trousers, giving full āCEO on a wine-tasting breakā energy. The look is finished with gold-accented jewelry, dark sunnies, and a glass of bubbly for that luxe touch.
2. Ā Cozy Neutrals and Leather Layers
The friend on the left is in a soft, long light-beige coat over a black base, keeping it simple and polished for a vineyard stroll. On the right, the other friend pairs a black leather jacket with dark pants and a big white scarf, adding that cool-girl contrast while still staying super snug with sunglasses and a glass of red.
3. Ā Classic Wool Coats and Relaxed Denim
On the left, sheās layered a long chocolate coat over a checked blazer, white blouse, straight dark jeans, and black knee-high boots for that effortlessly polished countryside vibe. Her friendās in a rich brown fur-front coat cinched at the waist with wide blue jeans, keeping it chic and cozy for castle steps and crisp air.
4. Plush Shearling Vest and Cream Knit Set
Sheās serving luxe ski-chalet energy in a chunky cream turtleneck sweater with matching knit joggers, topped with an oversized camel shearling vest. The look stays laid-back but elevated, perfect for sipping wine on the balcony while you take in those snowy mountain views.
5. Tweed Blazer and Riding Boots
Sheās going full countryside chic in a brown tweed blazer over a light turtleneck with slim dark trousers and tall brown riding boots. The matching cap and crossbody bag make it feel like the perfect outfit for wandering through a storybook village between tastings.
6. Chunky Shearling Jacket and Easy Denim
Sheās cuddled up in an oversized black leather shearling jacket layered over a chunky beige turtleneck and wide-leg dark jeans, the ultimate cozy fireside winery look. The furry throw and relaxed pose just add to that āweekend in a rustic chaletā vibe.
7. Fluffy Shearling Coat and Vintage Denim
Sheās curled up in a plush off-white shearling coat paired with straight-leg blue jeans, giving total cozy-luxe lodge energy. The soft ballet flats and classic quilted bag keep it feminine and polished, like you just stepped away from the fireplace for one more pour.
8. Tailored Gray Coat and Cream Monochrome
Sheās glowing in a long, structured gray coat layered over a cream cardigan and matching high-waisted pants, keeping everything sleek and tonal underneath. The pointed cream boots and layered gold jewelry make it feel like the perfect āsip wine, stroll cobblestone streetsā city-winery moment.
9. Ā Romantic Off-Shoulder Knit Maxi
Sheās wrapped up in a soft gray off-the-shoulder knit maxi dress that drapes perfectly while still keeping her warm. The deep red bag, matching Mary Jane heels, and ribbon in her hair pull the whole look into this dreamy, old-movie-walk-through-the-vineyards moment.
10. Chic Blazer, Turtleneck and Sleek Mini
Sheās giving city-winery glam in a brown tailored blazer over a black turtleneck and short skirt, finished with sheer tights and tall black heeled boots. The leather gloves and oversized sunnies make it feel extra polished, like sheās heading from tastings straight to a cozy dinner reservation.
11. Cozy Cream Knit and Flowy Midi Layers
Sheās gliding through the vines in an oversized chunky cream sweater over a tiered, flowy ivory midi dress, with tall dark brown boots peeking out for a soft, romantic vibe. The neutral palette keeps everything dreamy and effortless, like you just threw it on for an afternoon of sipping and wandering.
12. Warm Shearling Jacket and Soft Wide-Leg Trousers
Sheās serving luxe lodge energy in a caramel shearling-lined jacket layered over a slouchy beige knit and crisp white wide-leg pants. The coordinating brown hat and dark sunglasses make it feel polished but still super relaxed for golden-hour tasting on the lawn.
13. Houndstooth Long Coat and Denim Midi Skirt
Sheās bundled in a long black-and-white houndstooth coat layered over a black top and a front-slit denim midi skirt, finished with tall black boots. Itās that perfect mix of classic and cozy, like youāre ready for a full day of tastings and exploring the estate grounds.
14. Plush Faux Fur Jacket and Sleek All-Black Base
Sheās serving vineyard glam in a rich brown faux fur jacket over a fitted black top and long black skirt or pants, grounded with pointed black boots. The warm belt, mini bag, and slim sunglasses keep it looking super polished while she sips her red.
15. Cinnamon Faux Fur Vest and Classic Flared Denim
Sheās serving Napa-chic in a belted brown faux fur vest over a fitted black top and high-rise flared blue jeans, giving that snatched-yet-cozy silhouette. Pointed boots and subtle accessories tie it all together, like youāre ready for both vineyard views and an elegant lunch reservation.
16. Chic Black Coat and Playful Printed Pants
Sheās keeping it fun with a long black coat layered over a cozy beige turtleneck and slim leopard-print pants, perfect for adding a little personality to a tasting-day look. The minimal styling lets the print do the talking while still feeling warm and polished for wandering the winery.
17. Plush Fur Topper and Monochrome Wine-Dinner Look
Sheās all dressed up in a soft brown faux fur jacket over a fitted dark turtleneck, giving major cozy-luxe energy for a winery dinner. The matching headband, gold earrings, and simple makeup keep it elegant and warm while she sips her red by candlelight.
18. Cozy Checked Layer and Light-Wash Denim
Sheās keeping it casual-cute in a cream turtleneck with light-wash flared jeans, topped with a long brown coat and a draped plaid scarf for that layered, vineyard-weekend feel. The tan boots and sunglasses make it look like the easiest outfit to throw on for a sunny but chilly tasting day.
19. Tailored Houndstooth Coat and Statement Leather Boots
Sheās dressed for a fancy tasting dinner in a long, structured houndstooth coat layered over a black top and matching midi skirt. The sharp black over-the-knee boots make the whole look feel elevated and powerful, like youāre closing out the night with a reserve pour.
20. Chic Shearling-Trim Jacket and Sleek All-Black Base
Sheās bundled up in a belted black leather jacket with cream shearling trim over fitted black pants, creating that cool-girl, moto-meets-vineyard vibe. The slim sunglasses and simple accessories keep it minimal and polished, perfect for golden-hour tastings on the deck.
21. Cozy Cable-Knit Sweater With Dark Denim at the Vineyard
Sheās rocking a creamy cable-knit sweater with dark wash jeans, keeping things warm but still super put-together for a relaxed day of wine tasting. A printed neck scarf, casual belt, and simple jewelry pull everything together, while the setting and a glass of rosĆ© make the whole look feel extra dreamy.
22. Chic Houndstooth Blazer Over Sleek Black Knit and Wide-Leg Trousers
Sheās wearing a black turtleneck tucked into high-waisted black wide-leg pants, topped with a long houndstooth blazer for that polished, cozy-at-the-vineyard vibe. The look is finished with a sleek belt, minimal jewelry, and classic black boots for an effortlessly sophisticated winter winery outfit.
23. Plush Faux-Fur Jacket Over Sleek Black Midi Dress
Sheās wearing a soft, beige faux-fur jacket layered over a simple black midi dress, perfect for staying warm while still looking glam at the winery. The outfit is finished with taupe heeled boots and loose waves, giving the whole look a cozy-but-elevated winter feel.
24. Playful Knit Sweater With Gingham Midi Skirt and Denim Layer
Sheās rocking a cream graphic knit sweater tucked into a flowy gingham midi skirt, with a draped denim jacket adding that laid-back, countryside charm. Bold pink cowboy boots and a woven tote bring a fun, personality-packed twist that feels so cute for sipping wine among the orchards.
25. Elegant Camel Coat Over Sleek Black Knit Dress
Sheās rocking a fitted black knit dress topped with a tailored camel coat, creating the perfect polished vibe for an evening wine tasting. Loose waves, a glass in hand, and minimal accessories keep the look refined but still relaxed and cozy.
26. Cozy Taupe Sweater With Rich Chocolate Coat and Slim Jeans
Sheās wearing a soft taupe knit sweater tucked into light-wash skinny jeans, layered with an oversized dark brown coat for that luxurious, countryside-winery warmth. Tall brown suede boots, a structured bag, and a classic leather belt tie everything together into an effortlessly chic winter look.
27. Relaxed Cream Sweater With Flowy Satin Maxi Skirt
Sheās rocking an oversized ivory knit sweater half-tucked into a drapey champagne satin maxi skirt for a dreamy, romantic vibe. Brown knee-high boots and a wide-brim hat give the outfit a rustic winery twist that still feels super polished.
28. Monochrome Cashmere Cardigan and Knit Skirt Set
Sheās wearing a soft beige V-neck cardigan over a matching knit midi skirt, creating that ultra-cozy, luxe winter look. A wide-brim hat and fuzzy cream handbag make it feel extra elevated, like the chicest stroll-through-town aprĆØs-wine moment.
29. Sleek Black Top and Maxi Skirt With Shearling-Lined Aviator Jacket
Sheās rocking a black fitted top tucked into a long black maxi skirt for a streamlined, polished base. On top, sheās layered a cropped brown aviator-style jacket with cozy shearling lining, plus pointed black boots and a structured bag for the perfect refined winter winery outfit.
30. Glam Black Knit Dress With Luxe Faux-Fur Wrap
Sheās wearing a fitted black sleeveless dress with sheer black tights, cinched at the waist with a chic belt for that sultry, fireside-wine moment. A plush faux-fur wrap draped over her shoulders and a sparkly headband make the whole look feel very old-Hollywood aprĆØs-ski.
Final Thoughts
Winter winery style is really all about dressing smart while still having fun with your outfit. Think cozy layers, rich textures, and pieces that look just as good indoors as they do strolling through the vineyards.
With these 25+ winter winery outfits, you can sip, stroll, and snap photos without worrying about the cold or your look. Mix comfort with a little elegance, add your personal touch, and rememberāconfidence is the best accessory. After all, great wine deserves a great outfit.