Outfits for Wine Tasting: 8 Polished Picks

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A thoughtfully styled outfit can make your next vineyard visit a full-bodied experience. Whether wandering through wine country, snapping pics at a scenic winery, or sipping reds in the tasting room, what you wear matters. Think smart layers, breezy silhouettes, and shoes you won’t regret after hour three. 

To help inspire you, we’ve put together eight casual yet stylish outfits for wine tasting that balance comfort with polish. With help from this guide, your winery style will have you raising your glass without giving your hemline a second thought. 

What to wear at a winery: 8 wine-tasting outfit ideas

The best outfits for wineries are weather-appropriate, easy to move in, and elevated enough for strolls through a sunny vineyard or cozying up in a candlelit tasting room. And don’t worry if all your favorite vineyards have different vibes—we have polished outfit ideas for every season and setting. 

1. Sundress, denim jacket, and comfy wedges

You can’t go wrong with a sundress for a day in wine country. Choose a breathable linen or cotton midi or maxi dress in a floral or solid print. Layer with a denim jacket for morning chill or expected weather shifts, and you’ll have a stylish yet practical outfit. 

Wear walkable wedges or block-heel shoes to navigate vineyard gravel without compromising style. Complete the outfit with a crossbody bag to keep your hands free for sipping, and slip on some sunglasses that suit your face shape. 

This outfit is ideal for spring and summer Napa Valley or Sonoma visits. 

2. Turtleneck sweater, midi skirt, and boots

For fall wine tasting, embrace cozy layers with a fitted turtleneck sweater tucked into a corduroy, satin, or velvet skirt. A midi hemline is fashion-forward and protects against crisp vineyard breezes. Warm hues like rust and deep plum reflect the changing foliage.

Pair this look with a lightweight blazer, tights, and knee-high boots. This combination feels refined but relaxed—perfect for lounging on a patio under golden leaves. 

3. Peasant blouse, tailored shorts, and espadrilles

Channel cottagecore style with an off-the-shoulder peasant blouse. Choose a lightweight top with ruffles or embroidery, and pair it with tailored linen or cotton-blend shorts. 

Finish the outfit with espadrille shoes or woven sandals and a straw hat for sun protection. Make this your go-to look for visiting Napa Valley on hot days in July and August. 

4. Jumpsuit, hat, and block heels 

A well-fitted jumpsuit is a one-and-done solution for winery outfits year-round. Go with breathable fabrics in warmer months and thicker cotton or wool blends in winter. Add a belt to define your waist. 

Top this outfit off with a wide straw hat for sun protection in spring and summer, and switch to a wool fedora for fall and winter. Depending on the season, slip into low block-heel shoes or sleek boots. This look delivers for rustic farm-style vineyards, elegant estates, and everything in between.

5. Floral maxi dress, wide-brimmed hat, and sandals 

A flowy floral maxi dress and a wide-brimmed hat are practically a rite of passage in wine country style. This look is feminine, breezy, and ideal for seasonal blooms, sunny skies, and Instagram photo ops. 

Pair your maxi dress with flat sandals, a minimalist purse, and delicate gold jewelry to complete this spring and summer look. 

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6. Button-down blouse, wide-leg pants, and flats

This tailored ensemble is perfect for indoor tasting rooms and upscale winery restaurants. Start with a crisp button-down blouse in silk or cotton, and add wide-leg trousers in a neutral tone. On hotter days, swap the trousers for culottes. 

Finish off the look with flats or comfortable shoes that easily take you from indoor spaces to outdoor patios. This ensemble works beautifully in spring and summer but can also handle cooler fall days with a light cardigan or oversized blazer. 

7. Wrap dress, cardigan, and low heels

A wrap-style dress is flattering and flexible. For spring and summer, opt for light pastels or floral prints. In fall, go for richer tones, adding texture with knits or velvet and thick tights. A cardigan is your best friend when the breeze picks up. 

Pair this look with low heels or stacked sandals, depending on the terrain. It’s equal parts romantic and functional, made for golden-hour pours and vineyard strolls. 

8. Crochet top, linen pants, and strappy sandals 

For a free-spirited take on winery outfits, style a breezy, cropped crochet top from your favorite boho brand with high-waisted linen pants in a neutral tone. This effortless look is ideal for warm-weather wine tasting in Napa or Sonoma. Accessorize with flat or low-heeled strappy sandals, a wide-brimmed hat, and earthy jewelry. 

Find preloved attire for wine tasting on ThredUp 

Dressing for a day at the vineyard means picking pieces that feel as good as they look. The best outfits for wine tasting are stylish and functional, helping you stay comfortable and photo-ready from one tasting room to the next. 

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With ThredUp’s massive range of styles, sizes, and price points, finding your next winery outfit is easy. Whether you’re drawn to sleek silhouettes or boho brands like Free People, ThredUp is one of the best places to buy dresses and more online, all preloved and available at a fraction of typical retail prices. 

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Need a little help pulling it all together? ThredUp’s AI-powered Style Chat has your back with personalized outfit inspiration and real-time advice. You bring the wine country plans—we’ll help you dress for it. 

FAQs

What should you not do at a wine tasting?

Wine tasting is as much about etiquette as it is about enjoyment. Here’s what to avoid: 

• Wearing strong fragrances: Perfumes and colognes can interfere with the wine’s aroma, which is crucial to the tasting experience. 
• Overindulging: Pace yourself to fully appreciate each wine and maintain decorum.
• Pouring your own wine: Always let the host or sommelier serve you.
• Wearing white clothing: Accidental spills can happen, and darker colors are more forgiving. 

Are any specific colors or patterns recommended for wine tastings?

When it comes to dressing for a winery visit, think beyond just “Instagram cute.” Let the season and setting guide your outfit. In spring, lean into light pastels; summer is perfect for bold, vibrant hues; fall calls for warm, earthy tones; and winter? It’s all about jewel tones. Opt for breathable fabrics like cotton or linen to keep cool when the temps rise. And while patterns are fun, try to keep them subtle so the real star of the day (the wine) can shine.

Should I dress differently for an upscale winery?

Absolutely. Upscale wineries usually come with a more refined vibe, so it’s a good time to elevate your look. Think tailored dresses, chic blouses, or crisp button-downs. Footwear should be stylish and functional—closed-toe loafers or ankle boots for cooler weather, or practical heels and wedges when it’s warm. Don’t forget the finishing touches: a sleek watch or a statement necklace can take your outfit from casual to classic in a snap.

What do you wear to a winery bus tour? 

Winery bus tours are like a mini wine adventure, and comfort is key when you’re hopping from vineyard to vineyard. Dress in layers—start with a breathable top and bring a light jacket for when the breeze picks up. Since you’ll be on your feet, supportive shoes are a must. Choose wrinkle-resistant fabrics that can handle a full day of tastings and travel. And for accessories? Sunglasses and sunscreen are non-negotiable, and a hands-free bag like a crossbody or mini backpack is your best friend.

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