What to Wear to a Winery

There’s something about a winery that elicits an air of sophistication and old-world refinery. Yet, a trip to a winery is also an act of frivolity, fun, and is an accessible luxury.

When deciding what to wear, you should marry these two vibes (the sophisticated and carefree/frivolous), creating a practical, beautiful, and animated ensemble. 

Juxtaposition is the secret ingredient for winery attire. So when deciding what to wear to a winery, keep this in mind.

A vibrant floral slip dress paired with your favorite worn-in denim jacket is a great example of this. But beware of your footwear! With a classic combo like this, footwear is the defining factor. 

Is your style hip and sporty? Throw on a pair of sneakers. Do you prefer a more bohemian look? A simple, flat sandal is the way to go. Or, do you want to feel a bit glamorous? Toss on a pair of heels. 

Here’s an important warning: the stiletto is not your friend when visiting a winery. Instead, choose shoes with a block heel and a securing ankle strap. There’s nothing glamorous about muddy heels or falling and getting tangled in the grapevines (I really wish I wasn’t speaking from experience).

How to Dress For a Winery

The location of the winery is always an important factor when deciding what to wear. Perhaps you’re attending a casual winery or one that’s a little more high-brow. This should play a role in the outfits you chose. However, what’s more important is staying true to your personal style. 

You’re not required to wear a wide-brimmed boater hat simply because it’s trendy. As a general rule of thumb, any outfit you wear should be 20% reflective of your locale and 80% reflective of you. But don’t ever wear sweatpants though—yes I know they’re trendy but a winery is not the time nor the place. 

Yet, deciding what to wear to a winery shouldn’t be complicated. We’ve created this helpful guide to help you choose your best winery outfit. So check out the cool winery outfit ideas we’ve collected below.

And, after reading this article, you’ll know the following:

  • Outfit ideas for both men and women
  • Fashion tips to avoid
  • Winery wear for different seasons
  • What to bring to a wine tasting
  • How much to tip at a winery

20 Winery Outfit Ideas You Must Try

What to Wear to a Winery: Outfits For Men

What should I wear to a winery? That’s a good question. If you’re a man, you’ve got lots of options. And if you want to look suave, sophisticated, and like you fit right in with your surroundings, we’ve got some great outfit ideas for you.

When thinking about what to wear to a winery, you should also consider what season it is. So, with that in mind, let’s view these looks. 

Summer Winery Look #1

When in doubt regarding summer menswear, look to the Italians. This outfit is a classic, composed example of Italian high-summer fashion. A trim linen trouser, short sleeve, white button-down shirt, and chic sunglasses never go out of style and are appropriate in nearly every situation. 

The accessories are the more fashion-forward pieces here—including the top-detailed loafer, the detailed leather belt, and the classic hat.  

This outfit, while perfectly composed as is, can be altered to fit any style. You could omit the hat, add a more simplistic belt, fresh white sneakers, and the outfit will be completely transformed. So when thinking about what to wear to a winery in the summer, here’s the perfect look for you.

Summer Winery Look #2

The double print outfit—while this is one of my favorite looks, it’s not for the faint of heart. Summer is the perfect time to experiment with such a look. While undeniably bold, the minimal coverage of shorts and a short-sleeve shirt (versus a completely head-to-toe ensemble) makes this look more accessible for the average man.

While the double print doesn’t need to be floral, the black backdrop and muted colors of the print make this look quite wearable.

By adding the matching set with sneakers, the wearer has taken an outfit that could be construed as feminine and turned it into a look somewhat reminiscent of a soccer uniform. And who doesn’t want to look even a little bit like David Beckham?

Also, if you prefer casual winery outfits, as opposed to more fancy attire, this could be a look for you.

Summer Winery Look #3

Here we see a beautiful use of neutrals. This relaxed linen look offers both coverage and breathability for the warm summer months. The drawstring on the pants gives them a casual flair, making them almost like a jogger. And the loafer and button-down shirt ground the look, turning it into something chic as opposed to sloppy. 

By wearing gold-rimmed, classic round sunglasses and a simple gold necklace, he’s also added a touch of edginess and elegance to an outfit that likely feels as if he’s wearing pajamas. 

Autumn Winery Look #1

As we move into fall, transitional pieces are key. This man knows exactly what to wear to a winery in the fall. The heather white cotton hoodie, layered with a lightweight wool suit allows the wearer to transform his look as the day progresses.

When a chilly September morning evolves into a warm September afternoon, removing the jacket doesn’t make the outfit look any less complete.

Pairing the clothing with crisp white sneakers and a hoodie gives the outfit a casual flair. The wearer has also lessened the seriousness of a traditional suit. This allows him to enjoy a playful new take on a classic male staple.

Autumn Winery Look #2

This outfit has all black everything. Plus, the look is both incredibly edgy and timeless. The edginess can be found in the details—the almond-toe boot, the black steel watch, and the patent leather clutch.

The black jeans and sweater are staples, and the look is all woven together with the leather moto jacket, which is both a classic and iconic symbol of cool. 

This is a transitional outfit that can be altered by swapping the sweater for a white tee, the boots for sneakers, or fitted black jeans for faded anti-fit denim. This outfit and its components are a perfect example of chameleon dressing.

With these staple pieces in your closet, you’ll always have something to wear, whether you’re going to a winery in the fall or anywhere else. 

Autumn Winery Look #3

As the autumn progresses, getting chillier by the day, what you wear should change as well. By October, your white sneakers will be replaced with boots, your cotton sweaters replaced with merino wool sweaters, and your accessories will shift from sunglasses and hats to scarves and gloves. 

This combination of black jeans, top-stitched Chelsea boots, and a tweed overcoat is the perfect outfit for autumn. Plus, the addition of a colorful printed scarf and buttery chocolate brown leather gloves is what makes this outfit not only classic but also unique, because it reflects the man’s personal style.

Autumn Winery Look #4

The later into the season, the more layers are required. However, adding layers doesn’t mean you have to add bulk to your outfit. Pairing a fitted waffle knit henley with a shawl, and a collared cardigan—the color pictured is quite aptly named ‘wine’—is enough to keep you cozy throughout the later days of fall (think November). 

By adding a jacket and scarf, this ensemble is going to take you right through those winter winery days. So if you’re wondering what to wear to a winery when the temperature starts to drop, this outfit is a great choice.

Winter Winery Look #1

There’s something about male ‘winter winery wear’ that makes me think of the word ‘rugged.’ Now, I don’t mean backwoods Ron Swanson rugged, but a more refined and elegant take on the concept.

Not only is this flannel plaid jacket with a matching scarf an incredibly hip reinvention of a classic look, but it’s also going to keep you warm. 

Adding a toque (i.e. beanie) and layering some underpinnings will keep you toasty as well as stylish. The yellow high-top Converse shoes are an unexpected and delightful twist, although the wintry weather may demand something more practical, like an insulated boot. 

Winter Winery Look #2

If the rugged look isn’t your thing, this chic, monochromatic outfit may be the perfect option for a winter winery tour. This outfit is head-to-toe charcoal, yet each piece is a slightly different shade, creating a composed look without being stuffy. The turtleneck (along with the Barolo) is sure to keep you flushed and warm in chilly weather. 

The ‘turtleneck plus coat’ combination is the more sophisticated brother of the ‘hoodie plus blazer’ combination. It exudes class and style, so you’ll look and feel as bold and smooth as the wine you’re sipping.

Winter Winery Look #3

If it’s cold enough that a puffer is necessary, this is the way to make it ‘winery wear.’ The head-to-toe black ensemble elevates the utilitarian nature of the down-filled coat. The cropped pants, black socks, and sneakers add an edgy, cool, and sophisticated vibe to an otherwise simple outfit. 

By wearing silver accessories that coordinate with the exposed zipper, he has also managed to make the look quite glam. 

What to Wear to a Winery: Outfits For Women

What do you wear to a winery if you’re a woman? Luckily, there are more than a few options to choose from. So check out the outfits to wear to winery tours for women below. We’re sure you’ll love at least one of these looks.

Summer Winery Look #1

Summer winery wear is often the most fun to piece together. The above combination of a floral slip dress and white, silver buckle, detailed sandals is a pretty and simple option.

The addition of a baseball cap adds a hip vibe, as well as a practical component, for both sun coverage and the occasional bad hair day (it happens to the best of us).

If you tend to be a monochromatic dresser but want to try out the floral frock trend, a black-based floral print with white or gray details is a great option for you. 

Summer Winery Look #2  

Here’s another example of a printed summer dress that screams ‘winery wear.’ The bohemian print and ruffled sleeves have me dreaming of rosé wine already. If you lean a little to the Carrie Bradshaw way of life and require heels to breathe, then the thick-soled sandal pictured above is a great option for a winery. 

Accessorize this outfit with a saddle brown crossbody bag and a woven Panama hat and you’ll be the bohemian queen of the winery. Also, if you’re wondering what to wear to a winery and still look ultra-feminine, here’s your answer.

Summer Winery Look #3

Above we have two beautiful examples of ‘non-dress-based’ summer wine tour wear. The layers of neutrals and bohemian accessories make these outfits just as feminine as a dress, but perhaps a little more comfortable for those of you that prefer trousers. 

Here’s a suggestion: try swapping out those suede boots for a flat ivory sandal (and be very mindful when tasting the red wine).  

Autumn Winery Look #1

Now that we’re transitioning into fall, it’s important to marry your favorite summer pieces with some more grounding, autumnal pieces. This is September winery wear for the cool chick. The relaxed cotton hoodie and anti-fit pants—when paired with a sleek low-heeled boot and a refined leather belt—become elevated and incredibly wearable for a fall trip to the winery. 

If the hoodie feels too casual for you, swapping it out for a more tailored black blouse or pullover is a great option. Breaking up the black top and boots with ivory pants or white jeans is also an unexpected and polished look. Plus, you might as well get a little more wear out of those white bottoms before October. 

Autumn Winery Look #2

Here’s another great example of a transitional outfit that would be perfect for strolling through the grapevines and sipping on some wine. The dress, while lightweight and comfortable for those warm September afternoons, features the traditional fall colors of rust, orange, and black. 

The shoes, while a delicate suede, have a wooden block heel to save you from sinking into the soft ground. Plus the closed-toe-open-back style of the heeled slide is perfect for those early fall days.

The bag pictured, while larger than I might recommend for a winery tour, has a shoulder strap so your hands are free for tasting wine and taking selfies. So if you’re someone who can’t live without a large satchel, something like this is a great option.

Autumn Winery Look #3

What’s one of the best things about dressing in autumn? Tights! A chunky sweater dress is a cozy and comfortable option for a winery tour. When paired with tights (and this season’s most beloved shoe, the platform oxford), you’ll have a polished but relaxed look, which is perfect winery wear.

While the black tights and shoes ground the look, you could also pair a similar dress with a flat, over-the-knee boot for a similarly chic outfit. 

Autumn Winery Looks #4 & #5

Nothing is more quintessentially fall than a warm sweater. So if you’re wondering what to wear to a winery in autumn, a sweater should be your go-to choice. Above are two different outfits, styled with the same sweater. 

The first sweater is a cocoa brown funnel neck. Paired with suede leggings and a flat over-the-knee leather boot, this is a classic and sophisticated way to style a chunky knit. While monochromatic, the varying shades and textures of the pieces add depth to the look. 

The second option is the same sweater in an aloe green hue. Worn over a satin slip dress and paired with slouchy boots, it’s a slightly more feminine and romantic way to wear a fall knit. We all have our favorite fall sweaters and a fall winery tour is a perfect place to display them. 

If you’re lucky enough to tour more than one vineyard, your favorite sweater can make an appearance at both. You could wear it with suede leggings, tossed over a slip dress (or skirt), or thrown on with your favorite pair of jeans and pretty ankle boots. 

Winter Winery Look #1

Winter winery wear is all about layers. As I mentioned in the men’s section, you’ll want to be able to throw a layer on while outside in the cold, and take one off when inside, without sacrificing style. 

A great way to do this is by adding an overcoat over your leather jacket. If you have an oversized coat that will accommodate the extra layer, that’s perfect! If not, you can simply drape your coat over your shoulders as pictured above.

The accessories here are also ideal for wine touring. The flat leather boots and crossbody bag are both practical and match the sleek look. Here’s a tip: as seen above, make sure to layer your bag underneath your overcoat. This will give the look some depth, and keep your belongings extra safe (just in case you get a little tipsy). 

Winter Winery Look #2

Just like your cozy sweater is your fall go-to, the long-knit dress should be your winter go-to. Comfortable and warm, a long-knit dress is a glamorous way to essentially wear your favorite sweater—and feel like you’re wearing a blanket—out into the world. 

When paired with a block-heeled boot and crossbody bag as pictured above, this combination is ideal for traipsing around a cold winery. Adding a long overcoat and thick scarf will ensure you stay warm on a cold day, but won’t hinder the sophistication of the dress. 

Fashion Tips to Avoid When Going to a Winery

Now that you know what to wear to a winery, you might be wondering what not to wear. So here’s a list of what to avoid when dressing for a winery:

  • A massive handbag: Always opt for something smaller. Or, if you’re too attached to your mega-bag, be sure it has a crossbody strap to free up your hands
  • Heels: Now, I’m not as strict about this as some may be. As long as you’re an adept heel-walker and choose something with a block heel, you’ll be fine. But avoid anything with a slim heel, especially if it’s suede. Dirt is the mortal enemy of the slim suede stiletto. 
  • Overdressing: Yes, visiting a winery is a luxury, but leave the black-tie attire at home. 
  • Lipstick: Just don’t do it. Opt for a tinted lip balm instead. It will keep your lips better hydrated, offer a little color, and you won’t have to spend half your time in the ladies’ room reapplying it.
  • Tight, restrictive clothing: A winery tour is an opportunity to have fun and be a tad indulgent. Fussing with tight clothing or denying yourself charcuterie lest you pop a button is not what winery tours are for. 

What to Wear to a Winery in Different Seasons

What do you wear to a winery in different seasons? Just like any outing, the seasons (and weather) will define our style. So your winery wear should reflect the season as well as the temperature, which as we all know can be fickle.

Be sure to choose pieces that consider the practical aspects of each season, while always remaining true to yourself and your style.

What to wear to a winery in the summer?

The summer is my favorite time of year to visit a winery. There’s something about sipping a frosty, crisp glass of rosé while donning your favorite flowy dress, sandals, and sunnies that just sounds like heaven on earth. 

If you’re a lover of floral printed dresses like I am, now is the perfect opportunity to throw one on. If a voluminous frock isn’t your cup of tea, a monochromatic outfit (I’m currently in love with head-to-toe ivory or ecru) made up of cotton pants, a lightweight summer sweater, and sandals are just as glamorous and comfortable. 

What to wear to a winery in the winter? 

If you’re wondering what to wear to a winery in winter, there’s one thing to keep in mind. The most important aspect of your winter winery outfit is your footwear. 

It’s important to choose shoes that will keep you warm if you’re touring outside but won’t make you feel like you’re wearing your childhood Sorels when indoors. A sleek insulated Chelsea boot or a treaded platform combat boot are both great options. 

As for your clothing, the key here is layers. Don’t just toss on your parka and head out the door. A sweater, scarf, and wool coat will keep you just as cozy and looking much more stylish. If it’s particularly cold outside, a fitted down vest worn underneath your wool coat can add extra insulation without sacrificing style. 

What to wear to a winery in the fall?

A winery visit in autumn is the perfect opportunity to showcase your favorite, most luxurious knitwear. Whether it be an ivory, chunky cable knit crew or your most beloved black merino wool turtleneck, knitwear is the way to go. 

However, be mindful of the temperature. If it’s a warm fall day, it’s best to achieve this look with cotton-based knits to avoid overheating after that second glass of cabernet. 

Pair your knits with denim jeans or casual, comfortable trousers. If you happen to be visiting a winery in September, a black sweater, ivory cotton chino, and black closed-toe slides are beautiful, simple transitional outfits. 

Can I Wear Jeans To a Wine Tasting

The whole world is becoming more casual. So denim, when paired with the appropriate garments, is acceptable in pretty much any circumstance.

As I mentioned before, juxtaposition is the key to winery dressing. Pairing your favorite pair of cool, ripped jeans with a silk blouse and blazer is a great example of this.

Do Wineries Have Dress Codes?

Wineries do not have dress codes. However, they are beautiful establishments, often with a rich history and well-dressed staff. Dress code or not, I believe that an outfit should be reflective of the wearer as well as the destination. That means your outfit should reflect the ambiance and atmosphere of the winery. 

If you’re concerned about whether or not your chosen outfit is appropriate, I recommend looking at the establishments’ website and considering its aesthetic.  


What should I bring to a wine tasting?

Of course, choosing what to wear to a winery isn’t the only thing you should consider. You also need to figure out what to bring with you. So here’s a list of essential items you should bring to your next wine tasting.

  1. A small, crossbody bag is a must for a wine tasting. It will keep your hands free so you can eat the vino and cheese. Since your bag is small, you must be scrupulously selective about what you bring along. Your wallet and cellphone (for the necessary and inevitable selfies) are essential of course.
  2. A lightly tinted, hydrating lip balm will keep your lips plus and add a nice glow to your complexion, while also enhancing your overall look.
  3. Throwing a couple of Advils in your purse or pocket may be a good idea—for the somewhat inevitable headache which often accompanies the mixing of whites, reds, and rosés.
  4. Also, if you choose to ignore my warning about wearing stilettos, then maybe bring along some Band-Aids as well.

Can you get drunk at a wine tasting?

While it’s a free country and technically you can get drunk anywhere alcohol is served, a wine tasting is not the place nor time to do so.

A tasting is most definitely a place to have fun, but it is also intended to be a learning experience. It’s an opportunity to hone your sommelier skills and determine your preferences when it comes to variety, richness, and flavor. 

So, to get the most out of your visit, stick to small sips, enjoy the food pairings, and save the drunkenness for the pub. 

How much do you tip at a winery?

Tipping at a winery is not traditionally necessary. However, years in the hospitality industry have left me with the fervent belief that anytime someone is serving you, a tip is recommended (at least in North America). 

There’s a lot of thought and preparation involved in the service at a winery. The staff is trained to teach you about each specific wine, the process of making it, and how best to pair it with food.

So, in addition to regular hospitality duties, winery staff are offering you valuable information. In my opinion, a 20% tip is always appropriate and appreciated. 

Final Thoughts

Above all else, your personal style is unique. That’s why, ultimately, no matter what the season, location, or company, your winery wear should reflect you. And choosing what to wear to a winery truly is a personal choice.

When thinking about how to dress for winery tours, it’s also important that you’re comfortable—whether that means staying cool in the summer, warm in the winter, or being able to consume as much cheese as you’d like without fear of bursting a zipper. 

A winery tour is intended to be a fun, fabulous learning experience, and a special activity to do with your pals or your partner. So, if you feel great in what you’re wearing, whatever that may be, the wine will only taste sweeter (or drier, depending on your preference). 

Got any other burning fashion questions? Check out some of our other articles:

What To Wear To A Celebration Of Life

What To Wear To Disney World

What To Wear To A Baseball Game

Your email address will not be published. Required fields are marked *