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Winter Winery Outfit Inspiration—15 Looks That Set the Mood Beautifully

Visiting a winery during the winter months offers a unique charm. The crisp air, serene vineyard landscapes, and intimate tasting rooms create an ideal setting for outfits that are both warm and sophisticated. Winter winery attire often emphasizes comfortable yet refined pieces, focusing on textures and thoughtful layering.

Incorporating soft knits, well-tailored jackets, elegant tall boots, and a palette of neutral colors can result in looks that feel seasonally appropriate and effortlessly put-together. The following collection presents various winter winery outfit concepts designed to capture that relaxed yet polished aesthetic that the season naturally inspires.

Fringe Sweater and Leather Midi Skirt

_katiepeake - winter winery outfits
@_katiepeake

A cream-colored sweater with fringe detailing provides a soft, flowing contrast to a sleek black leather midi skirt. The ensemble is polished with heeled ankle boots and accented with gold jewelry, creating a look that is both cozy and refined, perfect for a winter winery experience.

Faux Fur Coat and Black Maxi Dress

samiraradmehr - winter winery outfits
@samiraradmehr

A luxurious faux fur coat adds a touch of opulence and warmth to a long, fitted black dress, lending the outfit a dramatic and cozy feel. A brown belt introduces definition, while pointed-toe boots elongate the silhouette. The addition of a mini designer bag and dark sunglasses completes the chic, winter-appropriate winery look.

Wool Jacket and Riding Boots

amybethvdl - winter winery outfits
@amybethvdl

Rich brown riding boots serve as the foundation for this outfit, paired with black leggings for a clean, streamlined appearance. A wool jacket brings a polished, tailored element, balanced by a soft white layer underneath to brighten the overall palette. The combination of varied textures and warm neutrals creates an inviting and classic aesthetic suitable for a winery visit.

Houndstooth Coat and Denim Midi Skirt

jasmine_makai - winter winery outfits
@jasmine_makai

A long houndstooth coat offers both warmth and structure, effortlessly layered over a dark top and a denim midi skirt. The skirt’s simple, straight cut complements the heeled black boots, which add height and sophistication. This blend of classic patterns and winter textures results in a relaxed yet polished ensemble for a day of wine tasting.

Textured White Gown and Faux Fur Wrap

kelseymerritt - winter winery outfits
@kelseymerritt

A long, textured white gown creates a striking winter silhouette, enhanced by a statement concho belt that introduces a Western-inspired flair. A faux fur wrap draped over the shoulders adds a layer of warmth and richness, while a wide-brim hat lends a polished, rustic finish. A sleek black clutch completes this elegantly understated look.

Cozy Knit Cardigan and Mini Skirt

ariannabaq - winter winery outfits
@ariannabaq

An oversized, soft white cardigan imparts a warm, relaxed vibe, providing a lovely contrast to a structured dark mini skirt. Sheer tights add a subtle textural detail, and tall brown boots ground the outfit with rustic charm. This combination feels inviting and perfectly suited for a cozy winery setting.

Faux Fur Jacket and Cream Trousers

ooliviamiller - winter winery outfits
@ooliviamiller

A deep chocolate faux fur jacket creates a plush and dramatic layer over soft cream trousers, establishing a rich winter color contrast. A taupe turtleneck adds essential warmth without overpowering the color scheme, while brown boots and a suede bag tie the earthy tones together. The resulting look is cozy, sophisticated, and ideal for a cold-weather winery excursion.

Shearling Vest and Cream Knit Set

kelseymerritt - winter winery outfits
@kelseymerritt

A comfortable cream knit turtleneck paired with matching pants forms an effortlessly relaxed foundation, enhanced by the addition of a cozy brown shearling vest. The interplay of warm textures feels inviting, especially against a winter backdrop, while oversized sunglasses add a contemporary touch. This outfit masterfully combines comfort with subtle style, perfect for a laid-back winery visit.

Brown Jacket and Knee-High Boots

beckiehart - winter winery outfits
@beckiehart

Warm brown tones define this look, with a soft knit top and a structured jacket creating a comfortably layered outfit. Light-wash jeans maintain a casual feel, while tall suede boots add height and a polished, rustic edge. A dark leather bag and round sunglasses tie the color palette together, resulting in an easy and stylish ensemble for a winery outing.

Tweed Set and Patent Knee-High Boots

ruxylle - winter winery outfits
@ruxylle

A matching grey tweed jacket and midi skirt form a sophisticated, monochromatic foundation with subtle winter texture. A black turtleneck provides a contrasting layer and structure, while glossy patent knee-high boots introduce a sleek, modern element. This combination feels refined and understated, making it a chic choice for an evening at a winery.

Off-Shoulder Knit Dress

maggie_mccormack - winter winery outfits
@maggie_mccormack

A chunky grey off-shoulder sweater dress provides cozy texture and a relaxed silhouette. The long sleeves and ribbed knit enhance warmth, while the exposed shoulder adds a subtle touch of elegance. The overall impression is effortless and inviting, fitting perfectly for a casual winter afternoon at a winery.

Knit Cardigan Set and Wool Hat

kelseymerritt- winter winery outfits
@kelseymerritt

Soft neutral tones define this ensemble, featuring a cozy button-front cardigan layered over a matching knit skirt for a sleek, elongated silhouette. A wide-brim wool hat adds a touch of Western charm, complemented by a plush cream handbag that introduces warmth and texture. The monochromatic palette maintains a refined aesthetic, making it ideal for a winery setting.

Cropped Wool Jacket and Leather Gloves

ooliviamiller - winter winery outfits
@ooliviamiller

A rich brown cropped wool jacket provides a warm and structured base, enhanced by fur-trimmed sleeves for added depth. Sleek leather gloves lend a refined touch, while black leggings and tall boots ensure a clean silhouette. An oversized cognac handbag ties the earthy tones together, creating a polished ensemble perfect for a winter winery visit.

Shearling Aviator Jacket and Black Maxi Skirt

amybethvdl - winter winery outfits
@amybethvdl

A cropped shearling aviator jacket offers warmth and structure, pairing seamlessly with a fitted black maxi skirt for a sleek, elongated silhouette. The monochrome base maintains a refined palette, while pointed black boots add a sharp finish. A small black handbag and narrow sunglasses complete the look with understated sophistication.

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