Stuck on what to wear for your winter wine tasting adventure? Sipping Cabernet in cold weather brings a unique style challenge.
You want to look sophisticated and camera-ready for those vineyard shots, but staying warm and comfortable matters too. From cozy knit dresses to chic layered ensembles, these 19 winter winery outfits will help you nail that wine country aesthetic without freezing between tastings.
Whether you’re heading to a rustic barn tasting room or an upscale estate, we’ve got outfits that blend style and practicality. Let’s raise a glass to looking fabulous while staying snug this winter season.
19 Cozy & Chic Winery Outfit Ideas for Winters That’ll Turn Heads
#1. Vineyard Chic Classic
This sophisticated ensemble masters the balance of wine country elegance and winter comfort. The structured plaid blazer in rich brown tones creates a polished foundation, layered expertly over a soft beige ribbed sweater that offers both warmth and style.
Crisp white jeans brighten the winter look while providing a striking contrast to the luxurious brown suede over-the-knee boots, which add drama while protecting against chilly vineyard breezes. The designer belt cinches the waist and adds a touch of luxury, while oversized aviator sunglasses bring celebrity-worthy glamour.
A sleek low bun keeps hair controlled during wine tastings, and the overall neutral palette photographs beautifully against both rustic barrel rooms and scenic vineyard views. This outfit transitions seamlessly from afternoon tastings to evening wine dinners, proving that winter wine country style can be both practical and photo-ready.
#2. Edgy Vineyard Vibe
This ensemble brings an urban edge to traditional wine country style, proving that winery fashion doesn’t always mean flowy dresses and heels. The cream turtleneck sweater offers cozy warmth while creating an elegant contrast against the sleek black leather jacket, which adds both style and protection from chilly vineyard breezes.
Fitted black jeans keep the look modern and practical for wandering through barrel rooms or climbing stairs to panoramic tasting terraces. The chunky platform boots add an unexpected twist to wine country fashion while providing stable footing on uneven vineyard paths.
Round sunglasses and flowing dark hair soften the edgy elements, creating a balanced look that works beautifully for both casual tastings and vineyard photo opportunities. The outfit captures that sweet spot between comfort and style, letting you focus on enjoying the wine rather than fussing with your clothes.
#3. Western Wine Country Cozy
This outfit brilliantly merges rustic Western charm with wine country sophistication, making it a standout choice for outdoor winter tastings. The oversized plaid shacket in cream and brown tones serves as both a stylish outer layer and a cozy shield against crisp vineyard breezes.
Underneath, a black turtleneck provides essential warmth while keeping the look sleek and put-together. Dark straight-leg jeans pair perfectly with black ankle boots, offering both style and stability for navigating outdoor tasting areas.
The black cowboy hat adds authentic Western flair while protecting from winter sun, and round sunglasses bring a touch of modern chic. This ensemble works beautifully for both rustic countryside wineries and upscale tasting rooms, proving that Western-inspired fashion can feel right at home among the vines.
#4. Sunset Sophistication
This ensemble captures the essence of high-end wine country style with a dramatic winter twist. The camel wool coat draped elegantly over shoulders creates a sophisticated silhouette while offering warmth for sunset vineyard strolls.
A black cable-knit sweater pairs seamlessly with tailored black shorts, bringing unexpected edge to traditional wine country fashion. The look reaches new heights with sleek black knee-high boots that add drama while protecting against chilly vineyard winds.
Round sunglasses and voluminous waves evoke Old Hollywood glamour, creating stunning photo opportunities against the golden vineyard backdrop. The monochromatic base with camel accents photographs beautifully in natural light, making this outfit a stunning choice for both daytime tastings and golden hour vineyard tours.
#5. California Casual Wine Tour
This laid-back ensemble brings a fresh take to winter wine tasting attire, blending casual comfort with thoughtful style elements. The oversized white button-down with billowy sleeves adds an airy elegance while providing coverage against sudden vineyard breezes.
Distressed denim shorts keep things relaxed yet chic, while cream ankle boots elevate the casual look and offer practical footwear for exploring dusty vineyard paths. A cognac leather crossbody bag adds a rich accent while keeping hands free for wine glasses and tasting notes.
The outfit masters that coveted California cool vibe, making it a smart choice for those warmer winter days when layers aren’t necessary. Beach-waved hair and minimal accessories complete this effortless look that works beautifully against the backdrop of sun-drenched vines.
#6. Cozy Sunset Sips
This ensemble embraces winter wine tasting with sophisticated comfort and seasonal warmth. The classic black sweater serves as a versatile foundation, while wide-leg khaki pants bring a modern twist to traditional wine country attire.
The standout rust-colored plaid scarf adds both warmth and visual interest, its rich autumnal tones complementing the golden hour lighting at outdoor tastings. Black sunglasses maintain that air of wine country chicness while protecting against winter’s low sun.
The relaxed yet refined silhouette works beautifully for both indoor tastings and outdoor vineyard exploring. This outfit strikes the right balance between casual and polished, making it a smart choice for those chilly evening wine tastings when comfort meets style.
#7. French Vineyard Elegance
This sophisticated ensemble channels Parisian wine country style with a modern twist. The tweed mini dress in classic black and white brings timeless elegance to vineyard visits, while its fitted silhouette creates a polished look against autumn vines.
Underneath, a black blouse with dramatic puff sleeves adds romantic flair and necessary warmth for winter tastings. The combination cleverly balances vintage charm with contemporary design, making it a stunning choice for upscale wine experiences.
Long, sleek hair and minimal accessories keep the focus on the dress’s beautiful texture and tailoring. This outfit proves particularly photogenic among the changing vineyard colors, working beautifully for both indoor tastings and outdoor vineyard tours in mild winter weather.
#8. Romantic Wine Tasting Allure
This sophisticated ensemble blends classic elegance with modern wine country style. The cream silk blouse with romantic balloon sleeves creates a feminine foundation, while the fitted black mini skirt with a subtle side slit adds contemporary flair.
Over-the-knee black suede boots not only bring drama to the look but offer practical warmth for winter vineyard tours. Loose waves and minimal accessories keep the focus on the outfit’s striking silhouette.
The black and white color palette photographs beautifully against both rustic barrel rooms and winter vineyard landscapes. This combination proves especially versatile for full-day wine experiences, transitioning seamlessly from afternoon tastings to evening wine dinners.
#9. Monochrome Vineyard Vibes
This chic ensemble marries contemporary style with wine country elegance through its thoughtful black and cream contrast. The plush off-shoulder black sweater brings cozy sophistication while offering warmth for crisp vineyard afternoons.
A cream mini skirt creates a striking contrast against the sweater and complements autumn vineyard hues. Black knee-high boots add both drama and practicality for exploring vineyard paths, while protecting against winter chills. A structured black handbag keeps essentials close while maintaining the outfit’s sleek aesthetic.
Flowing dark hair and subtle jewelry complete this look that transitions beautifully from tasting room to sunset vineyard photos. The outfit masterfully balances comfort with style, making it a smart choice for winter wine adventures.
#10. Modern Wine Country Luxe
This ensemble flawlessly combines casual sophistication with wine country comfort. A rich chocolate brown suede jacket adds warmth and texture while complementing the architectural elements of upscale wineries.
The crisp white tank provides a clean foundation, tucked into relaxed cream wide-leg jeans that bring modern flair to traditional wine country style. Layered necklaces add subtle sparkle without overwhelming the laid-back luxe vibe. The outfit strikes a beautiful balance between polished and approachable, making it suitable for both casual tastings and more upscale vineyard experiences.
Soft waves and minimal makeup complete this effortless look that works beautifully against both rustic stone walls and elegant tasting rooms, especially during golden hour when the neutral palette glows.
#11. Cozy Winery Weekend
This casual-cool ensemble nails the balance between comfort and style for laid-back wine tastings. A cream quilted vest layered over a chocolate brown long-sleeve top creates warmth without bulk, making it easy to adapt to changing temperatures throughout a day of tastings.
Light-wash distressed jeans bring a relaxed vibe while staying on-trend. Aviator sunglasses add a touch of glamour, perfectly complementing the effortless waves that catch the autumn light.
This outfit works wonderfully for casual vineyard hopping and outdoor patio tastings, especially during those crisp winter afternoons when layering is key. The neutral color palette photographs beautifully against rustic stone walls and autumn foliage, while maintaining that effortless California wine country aesthetic.
#12. Suede Sophistication
This outfit masters luxurious winter wine tasting style through rich textures and thoughtful layering. A dramatic brown suede long coat creates an elegant silhouette while providing warmth for vineyard exploring.
Underneath, a fitted black turtleneck pairs seamlessly with a camel suede mini skirt, creating a sophisticated foundation. Black tights and knee-high boots offer both style and practicality for navigating vineyard terrain in cooler weather. The tan leather handbag adds a coordinating accent while keeping wine tasting essentials close.
Sleek, straight hair and natural makeup complete this polished look that works beautifully from morning tastings through sunset vineyard tours. The earthy color palette harmonizes perfectly with autumn vines and golden hour lighting.
#13. Estate Wine Tour Elegance
This sophisticated ensemble captures the essence of luxury winter wine tasting at upscale estates. The dramatic navy wool coat sweeps elegantly to the ankles, providing both warmth and drama for winter vineyard visits.
A cream cable-knit turtleneck sweater adds rich texture while staying cozy for cellar tours and outdoor tastings. High-waisted black trousers create a sleek silhouette, tucked into brown leather boots that blend practicality with polish. The structured black handbag adds timeless sophistication, while retro-inspired sunglasses bring a touch of Old Hollywood glamour.
The bob haircut maintains clean lines that complement the outfit’s architectural elements. This look transitions beautifully from formal tastings to evening wine dinners at prestigious estates, proving that winter wine country style can be both practical and luxurious.
#14. Sweet Starlit Sips
This charming coordinated set brings playful sophistication to winter wine tasting adventures. The mocha brown knit dress adorned with delicate star embellishments creates a feminine silhouette while offering comfort for all-day tastings.
Cream knee-high boots add a modern touch while providing practicality for vineyard walks, their light color creating striking contrast against the darker dress. Oversized sunglasses bring Hollywood glamour to wine country style, while loose waves catch the golden hour light beautifully.
The outfit’s midi length works perfectly for outdoor tastings, offering coverage while staying stylish. Subtle jewelry and a natural makeup look complete this ensemble that transitions seamlessly from afternoon tastings to sunset toasts, especially lovely when photographed against autumn vineyard backdrops.
#15. High Fashion Vineyard Glamour
This show-stopping ensemble elevates wine country style to new heights. The metallic silver knit dress with geometric pattern hugs every curve while catching light beautifully against vineyard vistas.
Its high neck and long sleeves offer warmth without sacrificing style, while the scale-like pattern creates mesmerizing movement. Statement platform heels in classic black add drama and height, making legs look endless. A quilted black designer bag adds luxe sophistication while keeping essentials close.
The sleek updo with face-framing pieces maintains elegance while showcasing the dress’s intricate neckline. A gold statement watch brings warmth to the silver tones. This outfit commands attention at high-end wine tastings and special vineyard events, especially stunning against sweeping mountain views.
#16. Western Wine Country Rebel
This outfit turns heads by blending contemporary athleisure with bold Western flair. A black quilted vest paired with billowy white sleeves creates fashionable warmth for crisp vineyard days.
High-waisted black shorts add urban edge while cream and black flame-detailed cowboy boots make a dramatic statement against autumn vineyard scenery. The contrast between sleek athletic wear and statement Western boots brings personality to wine country style.
Long, straight hair softens the edgy elements while staying manageable during outdoor tastings. This ensemble proves wine country fashion rules are meant to be broken, working particularly well for casual tastings at modern wineries where traditional dress codes don’t apply.
#17. Sunshine and Sips Casual
This laid-back ensemble captures California wine country’s relaxed winter vibe perfectly. A chunky butter-yellow cardigan brings cozy warmth while adding a cheerful pop of color against the winter landscape.
Light wash wide-leg jeans create a comfortable, on-trend silhouette that works for all-day wine adventures. The camel-colored rancher hat adds both style and sun protection, while metallic loafers bring a touch of shine to the casual look.
A small blue crossbody bag keeps essentials handy without overwhelming the outfit. The combination masters that elusive balance of being put-together yet completely comfortable, making it an excellent choice for casual wine tastings and vineyard hopping when comfort takes priority over formality.
#18. Modern Retro Wine Tour
This sophisticated two-piece suit brings vintage-inspired glamour to wine country adventures. The cream and brown houndstooth pattern creates visual interest while maintaining elegance against pastoral vineyard backdrops.
Wide-leg trousers elongate the silhouette while offering comfort for vineyard walks, paired perfectly with a matching blazer that can be removed during warmer moments. Green pointed-toe heels add an unexpected pop of color while elevating the entire look.
A structured grey mini bag keeps essentials close without overwhelming the statement suit. Retro-inspired sunglasses and loose waves complete this ensemble that bridges past and present, working beautifully for high-end tastings and wine country photoshoots.
#19. Bold Sunset Sips
This playful ensemble brings dramatic flair to winter wine tasting with a modern cowgirl twist. The red mini dress with sweetheart neckline and puff sleeves makes a bold statement against green vineyard rows, while its empire waist creates a flattering silhouette.
White knee-high cowboy boots add unexpected Western charm while keeping legs warm during vineyard tours. Oversized sunglasses bring celebrity style to wine country, while tousled blonde waves catch the sunlight beautifully. This outfit masters the art of looking camera-ready while staying practical for outdoor wine adventures.
The striking red hue photographs brilliantly against both rustic barn settings and manicured vineyard backdrops, making it a showstopping choice for wine country social media moments.
