Make Your Winery Outfits Easy with These Timeless Ideas

Looking for the perfect winery outfits for every season? Look no further! This blog post has everything you need to know, from what to wear in the fall and winter to what to wear in the spring and summer. Plus, you will find tips on what to avoid, so you can look and feel your best on your next wine tasting adventure.

Why you should trust this guide

I live in Napa Valley, and my job as a wine copywriter and communications consultant takes me to California’s top wine destinations like Yountville, Sonoma, Sebastopol, and Healdsburg. Basically, I have a front row seat to all kinds of winery outfits when I’m out and about, and it’s easy to tell who has done their research, and who is winging it!

What to wear to a wine tasting is a breeze with this guide. Don’t forget to check-out these wine captions, quotes, and puns to use when you all about your trip on your Instagram!

Cute Winery Outfits for Fall and Winter

What to Expect When it Comes to the Weather

Fall is the best time to visit wineries in Napa Valley and Sonoma County, but September and October in Northern and Central California can see some dramatic temperature swings.

One day it will be 65 or 70, and the next it will be 85 or 90 degrees! While the days can still get pretty toasty in October, the nights are always chilly. No matter what outfit you decide to wear on your winery tour, always take a light jacket, a wrap, or a shawl with you.

Casual Dresses & Cropped Jackets

The most popular outfit you will see when you travel to wine country during autumn’s chilly months is a casual dress paired with a relaxed jean jacket. This is pretty much the unofficial uniform in Napa Valley and Sonoma County, regardless of the season.

If you don’t have a denim jacket, don’t worry. You can also swap for any cropped jacket or even use a cardigan sweater.

Long dress with black boots for winter winery outfit.

Dresses with Knee-High or Ankle Boots

Oh my gosh! I love this look. In my opinion the dress with knee-high boot look is one of the best fall wine tasting outfit ideas you can wear. You can wear short dresses, knee-length, tea-length, or long, flowy, maxi dresses.

Pull out your cowgirl boots, your leather boots, vegan leather or suede ankle boots for an outfit that says, I’m here to taste wine and have the time of my life!

Sarah Christine, of Sarah Styles Seattle, has created the most beautiful wine country dress with knee-high boots outfit.

Fall winery outfit with long sleeve dress and knee-high boots.
Image via Sarah Styles Seattle

Comfy Sweaters and Jeans

Who says you can’t feel cozy at your wine tasting? Timeless, relaxed elegance, versatility (you can dress sweaters and jeans up or down), and comfort. Add your favorite scarf, wear your hair up in a bun, put on a pair of earrings, and you’re ready to go. This is definitely at the top of the list when it comes to cute winery outfits.

Style these with tennis shoes, like Meghan from Wit and Whimsy (love her outfits!), or go with boots, ballet flats, or mules.

Grey sweater and jeans are a great fall winery outfit.
Image via Megan @ Wit and Whimsy

Cozy Neutrals

I love the way Amanda from Strawberry Chic layered this cozy neutral jacket with the denim and knee-high cream boots. So gorgeous for a fall wine tasting outfit that’s functional and stylish.

Fall winery outfit with neutral coat, cream boots and denim.
Image via Strawberry Chic

Spring and Summer Winery Outfits

Spring and summer are hot in California, and other popular wine regions. 100 degrees is not unheard of in August. Bring your sunscreen, wear light clothes, and stick to casual shoes like espadrilles, sandals (sparkly or leather), or sneakers.

Do you have a cute sun hat you’ve been dying to wear? Bring that too. It will help you look like a local when you walk through the vineyards on your tour of the winery.

Vibrant Dresses

Bright, poppy dresses are a must for your next winery outfit. Not only are dresses lightweight and easy to pack, but wearing a vibrant, colorful dress will produce some amazingly eye-catching photos.

Whether you’re standing in the vineyard among the green vines, or you’re sipping on the patio at a bucket list Napa winery, dresses are always a good idea in wine country.

Alicia Tenise has the most effortless summer style that looks so chic in the vineyard.

Colorful maxi dress in the vineyard: wine tasting outfit for summer
Image via Alicia Tenise

Shorts and Linen Shirts

The classic combo of linen shirts and shorts are an excellent choice for a summer winery outfit. Linen is super breathable, which will help keep you cool while you’re enjoying your wine tasting experience outside. The “quiet luxury vibe” of linen will have other guests wondering, does her family own the winery, or is she just visiting?

Jess Ann Kirby puts on a masterclass for this easy summer pairing.

A winery outfit idea for summer with linen shirt and shorts.
Image via Jess Ann Kirby

Pro Tips for Planning Your Winery Outfit

Avoid White

I don’t know about you, but the minute I wear white, the probability that I will drip or dribble something on my clothes increases by about a thousand percent. There will always be a red wine in your wine flight, so a good rule of thumb is to avoid white – unless you’re really, really careful with your sips.

Say ‘no, thanks’ to High Heels

Napa and Sonoma may seem glitzy on the outside, but really, these are rural, country places. With that in mind, you are going to encounter all kinds of surfaces when you go to a winery: gravel, pebbly paths, grass, and cobblestones.

Fall can also bring rain, and wet ground; and fallen leaves plus glasses of wine can make the ground super slippery.

If your wine tasting includes a tour of the winery and the grounds, definitely wear a flat shoe, or a wedge to make walking easy. You can even wear crisp white sneakers, if you dress them up a bit.

Avoid perfume and body lotion

One of the greatest joys a wine lover can experience when sipping is the aromas from the glass. Never, never, never apply perfume or scented body lotion before going tasting. This isn’t just for your benefit, but for everyone else in the tasting room or winery too.

Proceed with caution with bodysuits

Okay, real talk. It’s going to be a pain in the you-know-what to keep snapping and unsnapping the bottom of that bodysuit every time you go to the restroom. And, let’s be serious, after a few pours of wine, it’s going to get more and more annoying. While I love bodysuits as much as the next gal, I would probably skip these.

Tips

    • Be careful when you step into the winery’s vineyard for those cute Insta-pics. Late spring through early fall in Napa and Sonoma is rattlesnake season. And with temperatures fluctuating between the 80s and 90s during the day, those little buggers are still active. Be really careful when you take your vineyard outfit ideas into the actual vineyard rows, because these areas may contain rattlers. Even in towns with lots of foot traffic like Yountville or Healdsburg.
    • Fall, winter, and early spring can be rainy. If you travel to wine country during November to March, if possible, bring a pair of cute waterproof boots.
    • If you’re in a bind on what to wear, I’ve had really good experiences with Rent the Runway.

One of my favorite dresses I’ve worn out in Napa that I rented through RTR. Such a beautiful pattern.

Dress with autumn colors for a wine tasting outfit idea.

FAQs

Do wineries have dress codes?

Unlike restaurants, wineries do not have dress codes, but, here’s the thing: depending on the tasting room or winery you visit, you may want to put a little more oomph into your outfit.

If you’re going to a high-end wine tasting in Napa that is $200 a person, you will want to leave the jean jacket (and the denim) at the hotel room and opt for something just a bit more upscale.

On the other hand, if you’re checking out one of the laid-back, but fabulous downtown Los Olivos wine tasting rooms, you can get away with a cute flannel and knee-high boots combo, a fall dress, or just about anything, depending on the season.

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