These 25+ Winery Outfit Ideas Will Have You Booking a Tasting ASAP
If you’ve got a wine tasting on your calendar and no idea what to wear, you’re in the right place. Vineyard style is all about looking effortlessly put-together while staying comfortable enough to sip, stroll, and snap a few photos along the way. From breezy dresses to denim and boots, the vibe is casual, chic, and totally season-ready—whether you’re heading out in spring, summer, or that sweet in-between weather.
Below, I’ve rounded up winery outfit ideas that are easy to wear and even easier to love.
White dress & red boots
With a relaxed vibe and a touch of flair, this white sundress paired with vibrant red cowboy boots is a standout. The soft, flowy fabric of the dress balances the bold boots perfectly, creating an effortlessly chic look. Add in a straw hat and a glass of wine, and you’ve got the ultimate winery outfit for sunny days.
Eyelet Shorts & Black Tee
Classic with a warm-weather twist, this look keeps things effortlessly cool. The black fitted tee adds a sleek contrast to the white eyelet shorts, while the scalloped hem brings in a soft, feminine touch. A wide-brim sunhat and comfy flats finish off the outfit—easygoing and totally vineyard-ready.
Striped Sweater & Maxi Skirt
Soft textures and earthy tones make this outfit feel cozy but still warm-weather friendly. The oversized striped sweater layers effortlessly over a breezy white maxi skirt, adding movement and a relaxed feel. Finished with tan boots and a wide-brim hat, this look is great for sipping wine and strolling through the vines on cooler spring days.
Halter Top & Tiered Skirt
Flowy, textured, and full of charm—this halter top and matching tiered skirt combo brings a soft, romantic energy to the vineyard. The lightweight fabric moves with the breeze, while chunky black boots add a grounded, slightly edgy feel.
Floral Skirt & Tank Top
This outfit is all about laid-back charm with a pop of color. The sheer floral midi skirt brings a soft, feminine feel, balanced by a simple white tank that keeps things fresh and minimal. A straw tote and white slide sandals tie it all together for a look that feels easy, sweet, and totally spring-ready.
Button-Up Shirt & White Shorts
Timeless and effortlessly refined, this look leans into that understated old money aesthetic. The crisp blue button-up paired with high-waisted white shorts feels polished without trying too hard. Add in simple ballet flats, a structured straw bag, and vintage-inspired accessories for a clean, classic vibe that never goes out of style.
Related: 15+ Old Money Summer Outfits 2024: Casual Chic Summer Outfits
Backless Top & Lace Skirt
Chic and a little daring, this outfit is made for sipping rosé under the sun. The buttery halter top feels soft and elegant, while the sheer lace skirt brings in texture and movement. Styled with gold statement earrings and a sleek bun, it’s giving just the right amount of glam without going over the top.
Printed Skirt & Black Crop Top
Zebra print brings the drama, but the styling keeps it elevated. The midi skirt makes a statement, paired with a structured black crop top and a relaxed button-up layered on top. With pointed flats and a glass of white in hand, it’s sleek, playful, and just dressy enough for an afternoon at the winery.
Halter Top & Eyelet Pants
There’s something so clean and timeless about an all-white look—especially when it’s done with texture and shape. The crisp halter top feels tailored yet relaxed, and the eyelet pants add subtle detail without taking over. Paired with a brown shoulder bag and minimal gold accents, it’s a look that feels quietly luxe.
Printed Dress & Cardigan
Light layers make this outfit easy to wear from spring through late summer. The green floral dress is flowy and flattering, while the chunky knit cardigan adds texture and a bit of warmth when the breeze picks up. Finished with western-style boots and a wide-brim hat, it’s effortless and charming for any winery day.
Tie-Front Top & White Skirt
A little romantic, a little rustic—this look feels just right for golden hour in the vineyard. The tie-front top adds soft detail and shape, while the white skirt keeps things fresh and easy. Worn with tall tan boots, a woven tote, and a printed headscarf, it’s an outfit that feels both laid-back and thoughtfully styled.
Red Dress
Sunshine, wine, and a breezy red dress—honestly, that’s all you need. The soft silhouette and playful floral print make this one feel light and flirty, while the bold color adds just enough drama. Simple gold hoops and windswept hair keep it carefree in the best way.
Leopard Top & White Skirt
Leaning into something a little more statement-making? This look gets it just right. The deep-cut leopard halter adds a confident, luxe vibe, while the full white skirt keeps things soft and balanced. A matching headscarf, black clutch, and heels pull it all together—chic, unexpected, and totally wine-cellar worthy.
Printed Set & Cowboy Hat
Another fun take on winery style that blends bold and relaxed just right. The printed matching set brings movement and personality, while the cowboy hat and tall boots lean into western flair without feeling too overdone.
Floral Top & Pink Trousers
Bright colors and breezy vibes make this outfit a total standout for a sunny day at the vineyard. The floral tie-front top feels flirty and fresh, while the tailored pink trousers keep things feeling put-together without being too serious.
Red Sundress
Nothing says wine tasting in summer like a floaty red sundress. The relaxed shape and bold color make this one feel effortless and playful, while dark sunglasses and a classic shoulder bag give it a chic little edge. Easy to move in, easy to style—just add your favorite glass of rosé.
Chunky Sweater & Tiered Skirt
This outfit captures that in-between spring weather just right. The chunky knit offers a little extra warmth for cooler mornings, while the flowy white skirt adds a soft, airy feel that fits the season perfectly. Styled with western boots and a simple bun, it’s an easy look for slow days at the vineyard.
White Midi Dress & Platform Sandals
This outfit brings a mix of elegance and playfulness that works beautifully for a sunny day among the vines. The structured bodice and flared skirt give the white midi dress a polished yet twirl-worthy feel, while black platform sandals and layered pearls add a cool, unexpected contrast.
Red Dress & Sunglasses
Sunny skies and vineyard strolls call for something easy yet eye-catching. This bright red dress brings all the charm with its flowy fit, adjustable tie front, and breezy slit. Paired with tortoiseshell sunnies and a low bun, it’s the kind of outfit that feels confident without saying a word.
Blazer & Wide-Leg Trousers
This look leans into that effortless balance of polished and relaxed. The oversized blazer gives a tailored feel without looking too formal, especially when paired with breezy wide-leg trousers. Add a sleek bag, gold jewelry, and a subtle wave in your hair—and you’ve got an outfit that feels elevated but still totally easygoing for a day at the vineyard.
Tiered Lace Dress
Lace, ruffles, and ribbon—this look leans all the way into its feminine side, and it works beautifully. The layered silhouette creates such graceful movement, and the hair bow adds a sweet, vintage-inspired touch. It’s the kind of outfit that doesn’t need much else—just a glass of wine and golden hour light.
Tank Top & White Skirt
Easygoing but still put-together, this outfit feels just right for a casual wine day. The contrast of a simple black tank with a tiered white skirt keeps the look fresh, while classic sneakers make it practical for walking the vines. A straw tote and dark sunnies finish it off with that effortless countryside charm.
Floral Mini Dress & Cowboy Boots
Between the puff sleeves, lace-up front, and playful ruffles, this mini dress makes a sweet statement without trying too hard. The white cowboy boots give it a fun, country-chic edge that feels right at home among the vines. Add a pair of retro sunglasses and it’s one of those looks that just makes you smile.
Asymmetrical Top & Denim Skirt
This outfit brings a modern western twist to vineyard style. The asymmetrical top feels sleek and unexpected, while the high-slit denim skirt adds structure with a hint of edge. Finished with embroidered cowboy boots and oval sunnies, it’s a cool, confident take on wine tasting attire.
Cut-Out Dress & Straw Hat
This look feels like summer in the vineyard done right. The cream cut-out dress is flowy and feminine with just a hint of skin, while the wide-brim straw hat adds sun protection and timeless charm. Finished with dark sunglasses and black sandals, it’s easy, elegant, and ready for wine under a clear blue sky.
Two-Piece Set & Tall Boots
A little playful, a little bold—this two-piece set makes an entrance. The strapless top and ruffled mini skirt feel light and summery, while the tall brown boots and scrunched socks add just the right amount of contrast. With retro shades and a woven bag, it’s a vibe that bridges warm weather and early fall effortlessly.
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