What to Wear to A Winery: Picking the Right Outfit

You have a winery visit planned, but your closet feels like an empty abyss. Do not worry, I get it. Picking the right outfit for a day among the vines does not have to be a guessing game. I help you step out looking fabulous, comfortable, and ready to sip some delightful vino, without looking like you tried too hard or not hard enough.

Understanding the Winery Vibe

Each winery has its own personality, kind of like people. Some are super fancy, with white tablecloths and sommeliers who speak in hushed tones. Others are more like your chill backyard barbecue, just with better drinks.

You want to match the vibe. Showing up in a ball gown to a rustic farm winery might earn you some strange looks. Likewise, cutoff shorts at a high-end estate will not do you any favors.

Research the Winery

Seriously, do your homework. I always check their website or social media. I look at pictures of the place and pictures of other guests.

This gives me a good idea of what people typically wear. It also helps me avoid any embarrassing fashion faux pas.

Comfort is Your Best Friend

You are going to be walking. A lot. Through vineyards, perhaps up hills, and maybe even on gravel paths. High heels are a no for me, unless they are kitten heels and I know I will be mostly sitting.

You also want to be comfortable sitting, standing, and reaching for that next glass of wine. No one wants to be tugging at their clothes all day.

Footwear First

My number one rule for winery outfits is comfortable shoes. I learned this the hard way after one too many trips where my feet started screaming by lunchtime.

• Flats: Stylish sandals, espadrilles, or cute loafers are always a good choice.
• Wedges: A stable wedge gives you a little height without the teetering feeling of stilettos.
• Ankle Boots: For cooler weather, a chic ankle boot works perfectly and keeps your feet warm.

Please, I beg you, leave the stilettos for the club. Uneven terrain and fancy heels make a bad combo. I recall my friend, bless her heart, trying to navigate a gravel path in 4-inch heels. It was a spectacle, and not in a good way.

Layering: The Smart Strategy

Wineries, especially those in picturesque locations, can have unpredictable weather. Mornings can be cool, afternoons warm, and evenings chilly. This is where layering saves your day.

I always throw a light jacket or cardigan into my bag. This way, I am prepared for whatever Mother Nature throws my way.

Chic Outerwear Options

Here are my go-to layering pieces that look good and serve a purpose:

• Denim Jacket: A classic. It dresses down a more formal outfit or complements a casual one.
• Light Cardigan: Perfect for a slight chill or when the air conditioning in the tasting room is blasting.
• Blazer: If the winery leans a bit more upscale, a tailored blazer elevates almost any outfit.
• Shawl or Wrap: Adds a touch of elegance and warmth. Plus, it is easy to toss into a tote bag.

Fabrics: Breathable and Wrinkle-Resistant

Natural fabrics are your friend here. Cotton, linen, rayon, or a good blend. You want something that breathes, especially if it is warm outside. Nobody wants to feel sticky or look like they just ironed their clothes for a marathon.

Wrinkle-resistant fabrics are also a lifesaver. You will be sitting, standing, and maybe even leaning against a barrel. You do not want to look like you slept in your clothes before you even start tasting.

Color Palette: Earth Tones and Naturals

Think about the setting. Rolling vineyards, rustic barns, natural light. Earth tones, neutrals, and colors found in nature always look fantastic in this environment. I find they just blend in, in a good way.

Creams, olive greens, dusty blues, and terracotta shades look great. A pop of color is fine, but I usually avoid anything too bright or neon.

Outfit Ideas for Her

Here are some of my favorite outfit combinations, depending on the vibe of the winery and the weather.

Casual Chic Winery Look

This is my most common go-to. It works for pretty much any casual or moderately fancy winery.

• Flowy Sundress: Pick one in a breathable fabric like cotton or linen. Midi or maxi length is usually best.
• Jumpsuit: A comfortable, stylish jumpsuit is an excellent alternative.
• Denim Jacket or Cardigan: For layering.
• Espadrille Wedges or Stylish Flats: Comfortable and cute.
• Straw Hat: For sun protection and a touch of glam.
• Crossbody Bag: Keeps your hands free for wine glasses and snacks.

I remember one time I wore a super cute, flowy linen dress. It was perfect. I felt elegant but also completely relaxed. It was like the dress was made for sipping wine.

Upscale Winery Attire

For those fancier wineries where you might have a reserved tasting or a gourmet lunch.

• Midi Skirt and Blouse: A silk or satin midi skirt with a pretty tucked-in blouse.
• Tailored Trousers or Wide-Leg Pants: Paired with a sophisticated top.
• Dressy Jumpsuit: Something with a bit more structure or a luxurious fabric.
• Blazer or Chic Cardigan: To complete the look.
• Block Heels or Elegant Flats: Comfort is still key, even when dressing up.
• Clutch or Small Shoulder Bag: For your essentials.

I attended a special tasting once at a very exclusive winery. I wore a beautiful flowy palazzo pant in a deep jewel tone and a fitted cream silk top. I felt perfectly appropriate and stylish.

Cooler Weather Winery Outfit

Layering becomes even more important when the temperatures drop.

• Stylish Jeans: Dark wash or black jeans always look good. Avoid anything too distressed.
• Knit Sweater or Turtleneck: In a nice fabric like cashmere or merino wool.
• Ankle Boots: Flat or with a low block heel.
• Wool Coat or Trench Coat: For warmth and style.
• Scarf: Adds warmth and a pop of color or texture.

My favorite fall winery trip involved a cozy cable-knit sweater, dark wash jeans, and suede ankle boots. I was warm, comfortable, and ready for all the red wine tasting.

Outfit Ideas for Him

Gentlemen, you want to look sharp but not like you are heading to a board meeting. It is about relaxed sophistication.

Casual Winery Look for Him

This is the go-to for most casual to moderately formal wineries.

• Button-Down Shirt: Linen, chambray, or a classic collared shirt. Sleeves rolled up look particularly effortless.
• Nice Jeans or Chinos: Dark wash jeans or well-fitting chinos in a neutral color.
• Loafers or Stylish Sneakers: Clean, well-maintained kicks that are not your gym shoes.
• Light Jacket or Sweater: A sporty blazer, a light bomber jacket, or a nice v-neck sweater.

I once saw a guy at a winery in an ill-fitting t-shirt and baggy shorts. He looked like he got lost on his way to a backyard BBQ. Do not be that guy. A little effort goes a long way.

More Polished Winery Attire for Him

For those occasions when the winery calls for a slightly more elevated style.

• Sport Coat or Blazer: This immediately elevates anything.
• Dress Shirt: A crisp button-down, maybe a subtle pattern.
• Tailored Trousers or Dark Chinos: Well-fitting and pressed.
• Dress Shoes: Derbies or smart loafers.
• Polo Shirt: As an alternative to a button-down, for a refined casual look.

My partner always looks great at wineries in a casual sport coat over a crisp white button-down with dark jeans and loafers. He looks put-together without appearing stuffy, which is the perfect balance.

Accessories: Less is More, But Be Functional

You do not need to bedeck yourself in jewelry. Simple, elegant pieces are best. Think about practicality.

Accessory Type	Recommendation	Why This Works
Bags	Crossbody or small shoulder bag (for him, a small messenger bag or no bag)	Keeps hands free for wine glasses; easy to carry essentials.
Hats	Straw hats (for sun), fedoras, or wide-brimmed hats	Protects from sun; adds a stylish touch.
Sunglasses	Stylish, UV-protective pair	Protects eyes from sun; adds to overall look.
Scarves	Lightweight silk or cotton for warmth/style	Adds color/texture; can provide warmth if unexpected chill.
Jewelry	Minimalist necklaces, stud earrings, simple watch	Avoids catching on things; keeps focus on your outfit.

I always take a large tote bag too, just in case I buy some wine. It is much easier to carry bottles in a sturdy bag than trying to juggle them.

Things to Avoid

Just as important as what to wear is what not to wear. I have seen some real head-scratchers at wineries.

• Anything too revealing: Wineries are not clubs. Keep it classy.
• Anything too sporty: Unless you are literally going on a hike through the vineyards, leave the gym clothes at home.
• Brand new white shoes: Unless you enjoy scuff marks and dirt, choose shoes that can handle a little dust.
• Strong perfume or cologne: It interferes with the wine tasting experience for you and others. Your nose needs to focus on the wine, not your fragrance.

I once sat next to someone whose perfume was so overpowering, I could barely smell the delicate notes of the Pinot Noir. It was a shame, really.

The Golden Rule: Confidence

No matter what you choose to wear, wear it with confidence. If you feel good in your outfit, you will radiate that energy. And that, my friend, is the best accessory you can have.

So, go forth, choose wisely, and enjoy your delightful day among the grapevines. Sip, savor, and look fabulous while doing it. Cheers!

Frequently Asked Questions

Can I wear jeans to a winery?

Yes, absolutely. Dark wash, well-fitting jeans are perfectly acceptable for most wineries, especially casual or semi-casual ones. Just make sure they are clean and free of excessive rips or distress, otherwise you might look a bit out of place.

What about wearing white? Will I spill wine on it?

Wearing white is a personal choice. Yes, there is always a risk of spilling, especially red wine. If you are particularly clumsy or just want to relax without worrying about stains, consider off-white, cream, or other lighter neutral colors instead. I usually avoid wearing my absolute favorite white top, just in case.

Do I need to dress up for a winery?

It depends on the winery. Some upscale wineries with fine dining might warrant more formal attire like a blazer for men or a dressy midi skirt for women. However, most wineries are more relaxed, and a smart casual look is usually perfectly fine. Always check the winery’s website or social media to gauge their specific vibe.