What to Wear to A Winery: Ultimate Outfit Guide 2025
One thing about me is, I love a good winery day! Drinking a glass of wine, laughing with my girlfriends, and snacking on a charcuterie board is peak living IMO. And half the fun of planning a day of wine tasting is picking out what you're going to wear!
So today, I am sharing what to wear to a winery with over 20 classy and cute wine tasting outfit ideas that are easy to copy!
Whether you are taking some serious notes on your wine tours in Napa Valley, or just hitting up your local winery on a Saturday with some friends, these outfits will have you looking chic. (Just try not to spill any wine on them, okay? Keyword: try!)
What to Wear To A Winery: Spring and Summer
So I am organizing these outfits by time of year because you certainly won't catch me in a sun hat and and stylish sundress in the colder months! But, if you're planning your winery experience for the warmer months, then these outfit ideas I am sharing below will certainly fit the bill!
Romper and Jumpsuit Winery Outfits
In my opinion, stylish rompers definitely fit the winery dress code! I have rocked many a romper or jumpsuit to fit the wine country casual vibe in the Spring and Summer months.
The only drawback is the more wine you drink, the harder it might be to shimmy it back on after bathroom trips. So depending on how hard you go at the winery (no judgement here) it might not always be a great option. You've been warned.
Gingham Romper and Sandals
I love a good gingham print, and think a warm weather winery day is the perfect time to rock it! Paired mine with some chic sandals (and a wine glass of course)!
Floral Romper and Wide-Brimmed Hat
You can't go wrong with a floral print this time of year! And if you own a wide-brimmed hat and struggle to find occasions to wear it, well, a winery is the perfect place! Rock this with some sandals or comfortable shoes of choice and it's such an easy outfit to put together for a day of wine tasting!
Collared Jumpsuit and Sandals
I mean, so chic right? I love this vest / collared tank style jumpsuit look that is trending right now. Personally, I don't think wearing high heels is a good idea at a winery because you don't want the heel getting stuck in the ground, so I usually opt for a flat sandal!
Maxi Dress Winery Outfits
If you're looking for an easy outfit idea, a maxi dress is always a good choice! These spring and summer dresses are perfect for warm days and look so cute paired with some sandals! You can even throw on a light jacket or light sweater if it's going to be an all day affair and the temperatures are supposed to drop later on! It really is the perfect attire for a warm winery day!
Boho Print Maxi Dress
Boho chic looks are back trending this season and are a great choice for a more casual look that still feels elevated! This would look so cute with a cute straw crossbody bag. You could even rock this to a winery in the fall with a pair of ankle boots and a denim jacket! That's what's nice about these boho prints, they totally work for multiple seasons.
Floral Maxi Dress
You also can totally opt for a classic floral print maxi dress and you will fit right in with your winery style! This would look really chic with a sun hat and small handbag. Perfect for a super hot day of sipping some Rosé.
Denim Vest and Maxi Dress
I love adding a denim vest to a look for a trendy added layer of interest without overheating! This would be the perfect outfit to pack for a wine tasting trip because you could re-use the denim vest in other outfits as well since it's so versatile.
Skirt Winery Outfits
Rocking a skirt is always a good time, especially on a wine-tasting tour! A skirt outfit is a great go-to look for this time of year and there are so many good options on how to style them!
Personally, I like to keep my skirts long and flowy for a day at the winery because: wind happens and flowy skirts are just more comfortable in general! This way you can focus on having fun and not worry about your skirt flying up on you, especially since you'll likely be sitting outside!
Floral Maxi Skirt and One Shoulder Top
Such an easy look and the perfect way to look chic but still be comfortable for a wine tasting tour! Really any simple white top pairs well with a floral maxi skirt, but it's fun to add a bit of interest with a one shoulder, ruffle top detail, or unexpected neckline!
Midi Skirt Matching Set
Another way to rock a skirt is to get a matching skirt set! Such an easy but chic look. I love this one with the monochromatic earthy tones. And I think it looks so chic with these chunky but flat sandals. Perfect for a summer day at the winery! (Or even a beach vacation!)
Mini Dress Winery Outfits
Sometimes it's just so hot we want to rock a mini dress! But we wanna keep it classy too. I suggest sticking with a shift style or flowy style. Don't want to look like we're hitting up the club, but that we are semi-sophisticated wine connoisseurs (even if we actually aren't)!
Flowy Mini Dress Layered with T-Shirt
I think it's so fun to own an easy flowy mini dress that looks chic styled on it's own or layered with a t-shirt! Depending on how hot you get, the daytime temperature, or just what your personal style is, you can style a dress like this up for multiple scenarios!
Denim Shift Dress
Love a denim dress, but really any more structured material shift dress just screams classy to me in this silhouette! This is one of those classic looks that will make you feel chic in the best way as you are sipping your wine!
What to Wear to A Winery: In-Between Seasons
Getting dressed is hard when you're in that seasonal transition period! So I had to share some outfit ideas for if you're visiting a winery in-between seasons and the weather is not too hot, but also not too cold!
Let's make picking a chic outfit easy for you because the important thing here is that you feel comfortable and confident so you can have a great time drinking delicious wine.
Denim Jeans Winery Outfits
Yes you can rock a pair of jeans to a winery! I know I have! When the weather is mild and pleasant, you can totally class up your jeans to fit the vibe at a winery. Being confident in your late Spring or early Fall winery outfit with some stylish jeans as the base is a no-fail way to enjoy a lot of wine!
Denim Jeans and Sweater Vest
A sweater vest is the perfect thing to throw on with your jeans in-between seasons! Keeping it a neutral color means you can really wear it any time of year, and paired with some chic versatile shoes and accessories will make you the chicest one on the wine-tasting tours this season!
White Jeans and Denim Top
Denim on denim but with a twist! White jeans are super versatile and I strongly believe can be worn year round. However, you might want to skip the red wine with this look because the last thing you want is red wine stain on your pants.
Midi or Maxi Skirt and Sweater Winery Outfits
I love this combo for when the cooler temperatures start to crop up in the Fall or when things finally start to warm up a bit in the Spring! Check out these outfit ideas below that are all pretty similar, but fit this vibe that is perfect for sipping wine with your best friend at a winery.
White Cardigan, Floral Skirt, and Sandals
The perfect late Spring winery outfit idea! I love throwing on a floral midi skirt, sandals and a slouchy cropped cardigan. It's a never fail look that is effortlessly chic and looks so classy for a wine tasting day!
Monochromatic Black Sweater and Skirt
This is a great outfit idea for a Fall transition look! You could even throw a coat on over this and make it work in the winter. Keeping the whole look monochromatic from head to toe also ups the chic level.
Lightweight Sweater and Floral Maxi
Okay this one I am cheating because this is actually a sweater styled over a dress! But it looks like a skirt.
Definitely check out this blog post here if you're looking for more ways to rock a sweater over a dress and my best styling hacks!
Mini Skirt Winery Outfits
If it's in-between seasons, a mini skirt can be an easy option for looking chic but also comfortable. I think it looks so cute and there is a short window of time where these looks work during the year, so it's always fun to rock them when you can!
Mini Skirt, Jean Jacket, and Sneakers
Look #1 is perfect for a more Spring/Summer with the white sneakers giving it a warm weather vibe and the denim jacket giving it a more cooler weather feel!
Mini Skirt, Sweater, and Tall Boots
Look #2 is a great way to style a mini skirt for a mild Fall day! The sweater and boots and definitely scream Fall vibes, while the mini floral skirt is still a nod to the warmer weather.
What to Wear to A Winery: Fall and Winter
Last up, we have winery outfit ideas for when it's cold outside! Most likely you'll be siping your wine indoors or on a patio under a heat lamp! So you want to make sure you have a cozy chic vibe for enjoying your wine tasting in the Fall or Winter months.
Pants and Jeans Winery Outfits
Of course rocking a pair of jeans or pants is going to be a go-to in the colder months! These chic outfit ideas are all perfect for staying warm but looking cute while you are tasting wine.
Trousers and Sweater
Trousers have been a such a chic trend the past few years, and they fit right in paired with a sweater for a winter winery day! Love them paired with some chic ankle boots and a scarf coat.
White Jeans, Sweater, and Suede Jacket
Nothing looks chicer to me than a suede jacket! And like I mentioned before, white jeans are a vibe year round! This whole look is so perfect for a late Fall or early Winter day at the winery.
Denim Shirt and Denim Jeans
Denim on denim will never not be chic to me. I love adding the pop of burgundy with the shoulder bag and a pop of leopard with the mary-jane style ballet flats. This look is trendy but still a classic look that is perfect for wine tasting.
Plaid Poncho and Leggings
I feel like a plaid sweater poncho was made for a Fall winery day. If you want to look comfy but cute, pair it with some leggings and boots and it's a super effortless way to kind of sneakily wear a blanket as an outfit and we are not mad about it!
Sweater Dress Winery Outfits
This last category is for sure a classic for the colder months. Sometimes we want to level up and throw on a dress! When it's cold, a sweater dress is the perfect thing to wear so that you can feel classy and cozy during your Fall or Winter winery visit.
Sweater Dress, Tall Boots, and Wide-Brimmed Hat
The basic millennial Fall uniform. I feel like outside of a winery, these looks might start to feel a bit outdated in 2025, but at a winery? They're perfect!
Sweater Dress and Denim Trench
If you're going for a trendier vibe, then this is it for sure. The denim trench and burgundy boots make this look feel current and the sweater dress is the perfect neutral base. Also love this for a winter date night look!
Sweater Dress Layered Over Shirt Dress
This is such a fun look that will certainly keep you warm and looking classy chic. Definitely recommend a winter coat and accessories if it's extra cold out!
I hope you liked these practical tips on what to wear to winery no matter the time of year! Which of these looks is inspiring your most for your own wine tasting experience you have planned? Let me know all about it in the comments below.
Loved these outfit ideas and styling tips? Be sure to pin one of these images below on Pinterest to reference for later!
