How to Dress for a Vineyard in the Fall: 23+ Fall Winery Outfit Ideas to Recreate
Planning a trip to the vineyard this fall? The right winery outfit can make the day feel that much more special because sipping wine among the vines is just as much about the experience as it is about the look. The goal is something stylish yet comfortable, with pieces you’ll feel good in from the first tasting to the last photo opp.
Fall makes it easy to lean into cozy layers and rich textures. Think chunky sweaters with flowy skirts, sleek boots that handle a little grass, and jackets you can throw on once the sun dips. It’s about mixing those effortless staples with just enough polish so you look pulled together without feeling overdressed.
At the end of the day, vineyard style is all about ease. You don’t need an overcomplicated outfit, just the right blend of chic and practical to match the setting.
Ahead, you’ll find plenty of fall winery outfit inspiration to help you plan what to wear on your next visit.
Sweater & Midi Skirt
A simple sweater instantly feels fresher paired with a flowy gingham skirt. Add a denim jacket over your shoulders for a relaxed touch, then finish it off with red boots and a straw tote to keep the look casual but chic for a winery day.
Suede Jacket & Jeans
Suede and fringe are big this fall, and this outfit nails that effortless boho feel. A brown jacket over a crisp white tee and dark denim looks easy yet put-together. The cowboy hat and boots pull it all together with that subtle Western touch that’s everywhere right now.
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Black Blouse & Mini Skirt
A flowy black blouse always feels chic, especially tucked into a tailored mini skirt. The belt detail adds some interest, while tall black boots make the outfit sleek and winery-appropriate. A small crossbody bag ties it all together without overthinking it.
Chunky Sweater & Maxi Dress
An oversized cream sweater draped over a soft floral maxi dress makes the outfit feel both cozy and feminine. The flowy silhouette works well with rustic cowboy boots, giving the look an easygoing vibe that’s just right for sipping wine outdoors.
Knit Dress & Boots
A fitted knit dress always feels timeless, especially cinched with a slim belt for shape. Brown leather boots give it a classic fall feel, while the wide-brim hat adds that extra touch of winery polish. Simple, effortless, and easy to recreate.
Mini Dress & Tall Boots
A simple white mini dress feels elevated with tall brown boots. Draping a knit sweater over the shoulders adds a cozy layer without taking away from the clean look. Oversized sunglasses and a structured tote keep it chic but easygoing for a winery afternoon.
Turtleneck & Printed Pants
A neutral turtleneck layered under a long black coat creates an easy base, while the leopard print pants add personality and edge. The mix of cozy and bold makes the look stand out without trying too hard, keeping it stylish yet comfortable for a winery visit.
Turtleneck & Satin Skirt
A chunky knit turtleneck tucked into a camel satin skirt creates that perfect balance of cozy and polished. Black boots ground the look, while a quilted crossbody bag adds a classic touch. It’s an easy outfit formula that always works for a winery outing.
Jacket & Wide-Leg Pants
A lightweight brown jacket layered over a white top keeps things understated and chic. Wide-leg pants add a breezy touch, while the structured bag and gold jewelry elevate the outfit just enough for a winery visit.
Denim & Dark Neutrals
A denim jacket with wide-leg jeans and a simple white crop top feels laid-back but stylish. Next to it, the dark utility-style set with a shearling collar looks sleek and effortless. Both outfits get a cool edge from black boots and slim sunglasses, easy pieces that work well for a casual winery day.
Sweater & Satin Skirt
A light knit sweater tucked into an olive satin skirt creates an easy mix of cozy and polished. Brown boots ground the outfit and make it feel seasonal without overcomplicating things. It’s a simple pairing that always works for a day at the winery.
Tweed Dress & Blouse
Layering a sleeveless tweed mini dress over a black blouse makes the outfit feel classic with a touch of sophistication. The textured fabric gives it fall-ready polish, while the shorter hemline keeps it playful enough for a winery day.
Off-Shoulder Sweater & Midi Skirt
Instead of a typical knit, an off-shoulder sweater makes the look feel a little more playful. The suede midi skirt with a front slit adds texture and pairs effortlessly with tall black boots. A brown bag keeps the outfit grounded in warm fall tones.
Cropped Sweater & Mini Skirt
A cropped cable-knit in deep brown feels cozy yet modern when paired with a camel mini skirt. Cowboy boots finish it off with an easy fall vibe, making the whole look playful but still winery-ready.
Shearling Vest & Satin Skirt
A cropped white tee and flowy satin skirt give the outfit an effortless base. Layering a shearling vest on top adds warmth and texture, while snakeskin boots sneak in a fun twist. It’s a mix that feels casual but still polished enough for a winery visit.
Oversized Shirt & Wide-Leg Pants
An oversized button-up in a dark neutral feels effortlessly cool, especially paired with light wide-leg trousers. The slouchy fit makes the outfit easy to wear, while simple flats and a black shoulder bag keep it understated but chic.
Plaid Coat & Mini Skirt
A long plaid coat instantly elevates a simple mini skirt and tie-front blouse. Tall black boots make the outfit feel sleek, while oversized sunglasses and a structured bag give it that polished, city-meets-winery vibe.
Trench Coat & Knit Dress
A classic trench instantly sharpens up a simple black knit dress. Black ankle boots keep the outfit streamlined, while the long coat adds that polished, timeless edge that always works for a winery setting.
Oversized Sweater & Maxi Skirt
A slouchy red sweater paired with a printed maxi skirt gives an easy mix of comfort and charm. The warm tones feel seasonal, while simple boots keep the outfit grounded and practical for a stroll through the vines.
Utility Jacket & Mini Skirt
A beige utility jacket over a crisp white tee creates an effortless base. Paired with a black mini skirt and gold accessories, the outfit feels laid-back but elevated. Sunglasses finish it off with a cool, winery-ready vibe.
Matching Knit Set
A ribbed knit top with coordinating wide-leg pants makes an outfit that’s both comfortable and elegant. The all-black look feels sleek on its own, so simple shoes and understated jewelry are all it needs for a winery outing.
White Dress & Ballet Flats
An airy white mini dress with lace details feels fresh and feminine, while a blue headscarf adds a fun pop of color. Leopard print ballet flats bring in just the right amount of contrast, keeping the outfit playful but chic for a winery day.
Turtleneck & Leather Mini Skirt
A fitted black turtleneck tucked into a brown leather mini instantly feels polished. Sheer tights and pointed knee-high boots give the look a sleek finish, while a quilted clutch keeps it classic.
White Dress & Knee-High Boots
An embroidered white dress cinched with a wide brown belt feels crisp and put-together. Tall leather boots and a structured tan bag tie the outfit together, making it an easy option for a fall day at the winery.
Gingham Dress & Cowboy Hat
A gingham maxi dress gives off an easy countryside vibe, especially with its tiered silhouette. Adding a wide-brim hat and cowboy boots leans into the rustic charm, making it a laid-back yet stylish winery outfit.
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