Heading out for a day at the winery is always a special experience. Whether you’re planning a wine tasting with friends, celebrating an occasion, or just enjoying the scenic views, what you wear can truly enhance the entire vibe. The key is to choose outfits that blend style, comfort, and practicality—because you’ll want to look great while strolling through vineyards or lounging on the patio with a glass in hand.
When picking a winery outfit, think about the setting. Vineyards are often sun-drenched and breezy, with beautiful natural backdrops that invite photos at every turn. Your outfit should feel effortless but thoughtfully put together. It’s a chance to lean into relaxed elegance, where flowy fabrics, soft neutrals, and earthy tones feel right at home. And don’t forget practical details—like comfortable shoes for walking on gravel paths or a wide-brim hat to protect you from the sun.
In this guide, you’ll find over 25 winery outfit ideas designed to help you look and feel your best on your next vineyard visit. Whether you’re aiming for casual chic, a touch of romance, or timeless sophistication, these ideas will spark inspiration. Let’s explore some stylish combinations that work perfectly for winery adventures all year round.
25+ Winery Outfit Ideas
Flowy Maxi Dress with Straw Hat
A flowy maxi dress is a quintessential winery choice. Choose one with soft floral prints or muted earth tones that blend beautifully with the natural surroundings. The long, breezy silhouette keeps you cool and comfortable, especially on warm days. Pair it with a straw hat for added sun protection and an effortlessly stylish touch. Complete the look with flat sandals or espadrilles—perfect for navigating uneven paths while keeping your outfit elegant and relaxed.
White Linen Button-Down and High-Waist Shorts
For a crisp, clean look, go for a white linen button-down shirt tucked into high-waist tailored shorts. This combination feels fresh and airy, ideal for sunny afternoons among the vines. The breathable linen keeps you comfortable, while the tailored shorts add a polished edge. Accessorize with woven slides and delicate gold jewelry. A crossbody bag in a neutral tone keeps things practical and chic.
Midi Skirt and Sleeveless Blouse
A soft midi skirt paired with a sleeveless blouse creates a refined yet relaxed winery ensemble. Choose a skirt in a flowy fabric like chiffon or satin, and opt for a blouse with feminine details—think ruffles or subtle lace trim. This combination moves beautifully as you walk and looks great in photos. Add strappy sandals or block heels, and carry a lightweight cardigan in case the breeze picks up.
Wide-Leg Jumpsuit with Statement Earrings
A wide-leg jumpsuit offers easy sophistication with minimal effort. Look for one in a lightweight fabric with a cinched waist to create flattering lines. Solid colors like olive, navy, or blush work well in winery settings. Pair the jumpsuit with statement earrings to elevate the look without feeling overdone. Simple leather sandals and a small clutch bag complete this effortlessly chic outfit.
Floral Sundress with Woven Belt
A floral sundress instantly evokes a romantic vineyard vibe. Opt for soft colors like lavender, peach, or pale yellow that complement the surroundings. Add a woven belt at the waist to give the dress shape and definition. Pair this with flat sandals or wedges, and consider a lightweight scarf that you can drape over your shoulders if it gets breezy. This outfit is perfect for a casual tasting or picnic.
Cropped Jeans with Puff Sleeve Top
For a more casual yet stylish winery look, try cropped jeans with a puff sleeve top. The jeans keep the outfit grounded and comfortable, while the puff sleeve adds a trendy, feminine touch. Choose neutral or soft pastel tones for the top to keep things vineyard-appropriate. Pair this look with mules or low block heels, and accessorize with a tote bag for your essentials.
Knit Midi Dress and Ankle Boots
A knit midi dress is ideal for cooler winery days. It hugs the body in a flattering way while still feeling relaxed. Choose earthy colors like rust, olive, or cream for a sophisticated vibe. Add ankle boots to ground the look and make it practical for uneven terrain. A felt hat or crossbody bag in complementary tones adds the finishing touch, creating a look that’s both cozy and stylish.
Tiered Mini Dress with Denim Jacket
A tiered mini dress brings playful charm to your winery outfit. Choose one with soft ruffles or eyelet details for extra texture. Layer it with a classic denim jacket for warmth and laid-back style. Complete the look with espadrilles or flat sandals, and add simple hoop earrings to tie it all together. This outfit strikes a great balance between casual and cute.
Lightweight Romper with Crossbody Bag
A lightweight romper is perfect for warm winery days when you want ease and comfort. Choose one with a cinched waist and relaxed fit in a soft color or delicate print. Pair it with comfortable sandals and a crossbody bag to keep your hands free for wine glasses and snacks. Subtle jewelry like gold bangles or a layered necklace adds just the right amount of polish.
Pleated Skirt with Fitted Tank
Combine a flowy pleated skirt with a fitted tank for an effortlessly elegant look. The movement of the skirt adds visual interest, while the tank keeps the outfit grounded and simple. Choose neutral tones or soft pastels for both pieces to create harmony. Add strappy flat sandals and a wide-brim hat for sun protection and style.
Shirt Dress with Leather Belt
A shirt dress offers timeless appeal that works perfectly at a winery. Cinch it at the waist with a leather belt to create a flattering shape. This look can be dressed up or down depending on your footwear—go for ankle boots for a rustic feel or slip-on loafers for a preppy touch. Add a pair of oversized sunglasses for an extra dose of chic.
Boho Maxi Skirt with Crochet Top
Channel a relaxed boho vibe with a flowy maxi skirt and crochet or lace top. The mix of textures feels laid-back and romantic—ideal for a sunny afternoon at the vineyard. Pair the outfit with flat sandals or woven mules. Layer on a few beaded bracelets or a long pendant necklace to complete the look.
Wrap Dress with Wedge Sandals
A wrap dress is flattering on nearly everyone and easy to wear. Choose a lightweight fabric in a floral or subtle print. The wrap style cinches at the waist, creating a beautiful silhouette. Pair it with wedge sandals that add height while still being practical for outdoor settings. A small straw bag rounds out the look perfectly.
Wide-Leg Pants with Off-Shoulder Top
Opt for breezy wide-leg pants paired with an off-shoulder top for a chic yet comfortable winery outfit. The off-shoulder design adds a bit of flirtiness, while the wide-leg pants feel relaxed and easy to move in. Stick with light colors or soft prints. Add flat slides or espadrilles, and accessorize with layered necklaces for a polished finish.
Casual Jumpsuit with Canvas Sneakers
If comfort is your priority, go for a casual jumpsuit in a soft cotton blend. This all-in-one piece feels effortless and is easy to style. Pair it with clean white canvas sneakers for a sporty twist that’s still winery-appropriate. Add a crossbody bag and a denim jacket for cooler moments. It’s a laid-back look that still feels intentional.
A-Line Skirt with Button-Front Blouse
Pair a structured A-line skirt with a button-front blouse for a classic, feminine vibe. Choose a blouse with subtle details like puff sleeves or delicate embroidery. The A-line shape of the skirt flatters most body types and adds polish without being too formal. Add ballet flats or low heels, and finish with a small satchel bag.
Printed Kimono over Slip Dress
Layering a lightweight printed kimono over a simple slip dress creates a relaxed yet sophisticated look. The kimono adds color and texture, while the slip dress keeps things sleek and minimal. Pair this with flat sandals or slides and minimal jewelry. It’s a great outfit for transitioning from daytime tastings to evening dinners at the winery.
Cropped Sweater with Midi Skirt
On cooler days, try a cropped sweater with a high-waisted midi skirt. The cropped length keeps the proportions flattering and modern. Opt for a skirt in a soft fabric that moves well, like satin or lightweight knit. Pair with ankle boots or loafers, and add a structured bag for a put-together finish.
Utility Dress with Belted Waist
A utility dress offers a blend of function and style. The belted waist gives definition, while the structured silhouette feels effortlessly chic. Choose one in olive, khaki, or tan for a look that fits right in with the natural setting. Pair with flat sandals or boots, and accessorize with a simple pendant necklace.
Paperbag Shorts with Tank and Kimono
Paperbag shorts paired with a fitted tank and lightweight kimono make for a breezy, comfortable outfit. The paperbag waist adds detail and interest, while the kimono brings color or pattern to the mix. Flat sandals or slides keep things easy and stylish. Add a straw tote for a practical and polished touch.
Slip Skirt with Graphic Tee
For a casual-cool vibe, style a silky slip skirt with a tucked-in graphic tee. The mix of dressy and relaxed pieces feels modern and fun. Choose muted colors or soft prints for both items so they complement the vineyard setting. Add white sneakers or flat sandals and a denim jacket for a layered look.
Peasant Blouse with Distressed Jeans
A peasant blouse with soft embroidery or lace paired with distressed jeans strikes the perfect balance between relaxed and romantic. Choose jeans with minimal distressing to keep things polished. Pair with flat ankle boots or sandals. Simple gold hoops and a slouchy bag complete this down-to-earth look.
Gingham Dress with Flat Sandals
A gingham dress brings playful charm and vintage appeal to your winery outing. The checkered pattern feels fresh and summery, especially in classic shades like navy or red. Pair it with simple flat sandals and a crossbody bag. A delicate bracelet or two is all you need to accessorize this cheerful look.
Cropped Cardigan over Tank Dress
Layer a cropped cardigan over a fitted tank dress for a cozy yet chic winery outfit. The cardigan adds warmth and texture, while the tank dress keeps the look sleek and minimal. Pair with ankle boots or loafers, and add a crossbody bag for convenience. A few dainty rings or earrings add just the right touch of polish.
Lightweight Blazer with Tailored Shorts
For a tailored, slightly preppy winery look, try a lightweight blazer over a simple tank, paired with high-waist tailored shorts. This combination is polished yet comfortable, ideal for winery tours or tastings with a bit of formality. Pair with loafers or flat sandals, and add a structured bag for a smart finish.
FAQs
What should you not wear to a winery?
Avoid overly formal attire, sky-high heels, or anything too tight or restrictive. Comfort and ease of movement are key, especially if you’ll be walking outdoors or touring the vineyard.
Can you wear jeans to a winery?
Yes, jeans can work well at a winery, especially when styled thoughtfully. Opt for clean, well-fitted denim, and pair with feminine or polished tops to keep the look elevated.
Are hats appropriate for winery visits?
Absolutely. Wide-brim hats or straw hats not only look stylish but also provide sun protection—perfect for outdoor tastings or vineyard strolls.
What shoes are best for a winery?
Comfortable flats, sandals, espadrilles, or low block heels are ideal. Avoid stilettos or thin heels that can sink into grass or gravel.
Do wineries have dress codes?
Most wineries don’t have strict dress codes, but business casual or smart casual attire is typically recommended. Aim for polished but comfortable pieces that suit the setting.
Conclusion
Your winery outfit sets the tone for the entire day—combining comfort, style, and a little bit of personal flair. Whether you prefer a breezy maxi dress, chic tailored shorts, or a cozy knit midi, there’s no shortage of ways to look great while sipping your favorite vintage. The key is to choose pieces that make you feel confident and relaxed, while also being practical for the setting. Soft colors, flowy fabrics, and stylish accessories will always serve you well on a vineyard adventure. With these outfit ideas as inspiration, you’ll be ready to enjoy your winery visit in style, creating memories—and photos—you’ll cherish.
