What to Wear to a Winery for a Stylish Day Among the Vines

The first time I stepped onto a vineyard, I felt underdressed. The air smelled of grapes and oak, couples were laughing over their glasses, and I was there tugging at my outfit, wishing I’d planned better. It wasn’t about vanity—it was about belonging.

That moment stuck with me. Dressing for a winery isn’t about being picture-perfect; it’s about feeling like you fit the scene while still being yourself. When your outfit balances comfort and style, the whole experience changes—you move easier, smile wider, and stop worrying about what others might think.

Whether it’s a sunny afternoon in Napa or a cool evening in Tuscany, what you wear shapes how relaxed you feel.

So let’s break down how to dress for a stylish day among the vines—where every outfit detail helps you savor the wine, the scenery, and the moment a little more.

Know the Setting Before You Pick Your Outfit

Every winery has its own rhythm. I’ve learned that vineyards have personalities—some whisper luxury, others feel like backyard gatherings.

Napa’s vineyards lean polished, Tuscany loves relaxed romance, and small-town wineries keep things laid-back. What feels right in one place might feel out of step in another.

According to Lonely Planet, many Napa tastings now require reservations, and the setting can range from cellar cool to open-air terraces.

That means your outfit should balance comfort with presentation. Lightweight pieces that move easily and layer well make all the difference when the evening breeze rolls in.

Before you go, check the vineyard’s website or confirmation email for dress hints. A quick look at event photos often reveals whether guests favor sundress casual or blazer chic.

Next time you plan your visit, picture yourself walking through gravel paths, pausing under leafy vines, and taking photos in the afternoon sun. The right outfit should make each of those moments feel effortless.

Before you even open your suitcase, imagine where you’ll be sipping—it changes everything.

Dress for Comfort and Class

A winery outfit doesn’t need to shout “fashion blogger.” It just has to look relaxed and feel right.

Travel + Leisure recommends breathable fabrics such as linen or cotton blends that move comfortably through tastings.

These materials photograph beautifully and handle temperature changes far better than synthetics.

Many guests forget about spills. Darker shades, earth tones, or subtle prints can save the day if a swirl goes sideways. Pair them with easy silhouettes that don’t cling after a few glasses of rosé.

You’ll enjoy every tasting more when you’re not distracted by pinching shoes or sticky fabric. Once you’ve got comfort sorted, season matters more than you might think—let’s move to that next.

Winery Outfits by Season

Winery fashion shifts with the season, just like the vines themselves.

In spring and summer, airy fabrics and soft prints keep things fresh. Picture a wrap dress with espadrilles or light trousers and a sleeveless blouse.

Visit Napa Valley points out that daytime tastings can warm up fast, while evenings cool quickly. A denim jacket or cardigan keeps you comfortable once the sun dips.

In fall and winter, vineyards change color and mood. Muted leaves, golden light, and cooler air call for cozy layers like light knits, ankle boots, and tailored coats. Earthy hues blend beautifully with the scenery and photograph well too.

When packing, focus on pieces that layer easily. A single scarf can shift your outfit’s tone and keep you warm when the breeze arrives.

Once those layers are set, the finishing touches—your accessories—tie the look together.

Accessories That Work With the Setting

The secret to winery accessories is balance—stylish enough for photos but practical enough to carry you through the day.

A crossbody or mini tote keeps your hands free while tasting. Sunglasses and wide-brimmed hats protect against glare, while simple gold hoops or a slim necklace add polish without fuss.

Visit Temecula Valley reminds guests to skip perfume, since heavy scents interfere with tasting aromas. You want your nose focused on the notes in your glass, not your wrist.

Keep accessories minimal but meaningful—you’ll look refined without feeling weighed down. And just when you think you’re done, remember: the wrong shoes can undo the perfect outfit.

The Winemaker’s Secret: Shoes Can Make or Break Your Day

If there’s one thing that separates first-timers from seasoned tasters, it’s footwear.

NapaValley.com reminds visitors that “wine country casual” is about comfort, not couture. That means skipping thin heels and choosing wedges, loafers, or low-block sandals that handle gravel and grass with ease.

You’ll walk on uneven paths, step between vines, maybe even dance under string lights. Take it from me—pack a pair of foldable flats if your evening plans stretch past sunset. You’ll be grateful when the tour turns into a stroll under the stars.

Every step should feel natural and light—that’s the real definition of vineyard chic.

So now that the details are handled, here’s how it all comes together for winery events.

How to Dress for a Winery Event

Winery events add a little sparkle, but the approach stays simple: clean lines, soft tones, and comfort that lasts.

For brunches or daytime tours, smart casual always works. For weddings or dinners, go with a neutral jumpsuit, a structured blazer, or a soft midi dress. Pick fabrics that breathe, shoes that won’t sink into grass, and accessories that move easily from daylight to candlelight.

The best-dressed guests aren’t the flashiest—they’re the ones who look comfortable in their own skin. If I could redo that first winery day, I wouldn’t change the wine—just the shoes.

Before you pack your bag or plan your tasting route, let’s clear up a few quick questions that pop up often.

These are the little details that can make or break your day—what to wear, what to skip, and how to feel confident the moment you step onto the vineyard.

FAQ: What to Wear to a Winery

Can you wear jeans to a winery?

Yes, absolutely. Visit Napa Valley mentions that “wine country casual” often includes jeans, especially when paired with a blouse or button-down shirt. Just keep them clean, fitted, and in a darker wash for a polished look.

Are heels a bad idea for wine tastings?

Most vineyards have gravel paths or grassy lawns, so heels can make walking tricky. Napavalley.com suggests wedges, loafers, or stylish flats instead—comfortable shoes let you move easily and stay relaxed all day.

What kind of bag should I bring?

Go for a small crossbody or tote. You’ll want free hands for holding your glass or taking photos. A structured mini bag keeps your essentials close without weighing you down.

Can you wear perfume to a winery?

It’s best to skip it. Both Visit Napa Valley and Visit Temecula Valley warn that strong fragrances can interfere with tasting aromas. You’ll enjoy the experience more when the only scent in the air is the wine itself.

What colors look best in vineyard photos?

Earth tones and soft neutrals always work well—think olive, tan, cream, or rust. They complement the natural backdrop and photograph beautifully in golden light.

How should men dress for a winery?

Men can keep it simple: chinos or dark jeans, a casual button-down or polo, and loafers or clean sneakers. Add a light jacket if the weather calls for it.

Conclusion

Wine tasting isn’t about getting the outfit perfect—it’s about feeling comfortable enough to be fully in the moment. Whether you’re standing under string lights or walking between the vines, what you wear shapes how much you enjoy the day.

If this guide helped you plan your winery outfit, I’d love to hear from you. What’s your go-to look when you’re sipping among the vines? Drop a comment below—I might just feature your tip in my next post.