There’s just something special about sitting out and sipping on a glass of wine (or two) with some friends on a sunny Saturday afternoon. I love going wine tasting with my girlfriends and trying out different wineries for birthdays, events, or even just for the weekend. I recently went to Nashoba Valley Winery in Bolton, MA and had so much fun!
Some of my other favorite wineries / vineyards to do a wine tasting at are Truro Vineyards in Cape, Cod MA and Diamond Hill Vineyards in Cumberland, RI. And, of course, Napa Valley is on my “wine tasting experience” bucket list!
In all seriousness, do you guys call it a winery or vineyard? It’s a serious debate for me! I couldn’t tell which it should be called when I was writing this blog. Anyways, if you plan on treating yourself to a day of wine tasting, we’ve got something important to discuss—the wine tasting outfits!
Today, I’m showing you one of my favorite wine tasting outfits along with a few styling tips for what to wear when you go wine tasting. If you’re looking for cute and easy outfits on a budget, you’ve come to the right place. Let’s dive in!
*This post may contain affiliate links, which means I may receive a small commission, at no cost to you, if you make a purchase through any links!*


outfit details: bohemian dress (this has since sold out, shop here for a similar style) // taupe booties (these have since sold out, shop here for a similar style) // lipstick
Wine Tasting: Styling Tips for Your Next Day Trip
Make sure to follow me on Instagram for a try-on of all these items under my highlights and more Amazon fashion finds! If you don’t have Instagram, don’t forget to check out my Amazon storefront with even more Amazon fashion that I love!
Dress for the time of year you’re going in.
It really does matter the season—even if you go in winter and the winery has heated tents or indoor experiences, you still want to dress accordingly. Breathable fabrics (like linen pants) are ideal in the spring and summer. For the fall and winter, look for cozy textures to keep you warm. Check out a few different outfits I’d wear depending on the season!
Winter Winery Outfits









Fall Winery Outfits
















Summer Winery Outfits












Spring Winery Outfits








Light-colored clothes are chic, but be mindful!
You may want to wear white or light-colored clothes because they’re sooo good at instantly making you look chic, but, you’re probably better off skipping them if you’re clumsy (guilty!). As affordable as these pieces are, you don’t want a huge wine stain to ruin anything.
Comfortable shoes are a must.
Wineries consist of things like grass, gravel, and maybe even some cobblestone. Not only will the right pair of comfortable shoes keep your feet from aching, they’ll also keep you safe walking on rocky terrain (literally, lol). With any of the looks I referenced above, you can totally switch them out with block heels, ankle boots, or even stylish sneakers are a great option.
Don’t feel like you have to wear a dress, jeans are acceptable!
Even though I included (mainly) dresses in my seasonal wine tasting outfit inspo, you can still wear jeans and look cute. Dark wash denim will always take the cake for creating an upscale, high-fashion look. This outfit is the perfect example of how simple pieces can create a stunning look.

Layer lightly to stay cozy and stylish.
Adding on light layers to your look is never a bad idea, especially if you’re planning a wintery winery visit—or a fall/spring visit when transitional temperatures are in full swing. A knit sweater can elevate a winter look, and a light cardigan would look super cute over a maxi dress in the spring or fall.
Check out this post for tons of affordable knits and cardigans!
Find the right accessories to complement your outfit.
You want accessories that fit the season, make a statement, but don’t feel in the way. Let’s start with the most important accessory—sunglasses. These are a must-have for any time spent outdoors. If you’re wine tasting in the spring or summer, bring a chic wide-brimmed hat. Not only is it great for sun protection, but it adds to your whole summery aesthetic!
For the colder months, add a cute scarf to your outfit. Don’t feel like you have to wear anything super chunky and heavy, otherwise it can get in your wine glass juggling adventures. Something like this cute infinity scarf is perfect.

Dress in a way that feels authentic at you.
Wine tasting feels glitzy and glam, but don’t feel like you have to wear something that doesn’t feel like you. Wine tasting is always the perfect excuse to dress up a little, but have fun with it your way! Lean into your aesthetic, wear patterns that you feel comfortable in, and have fun with it.
Don’t forget about wearing the right lip products.
This tip is sooo underrated, and I feel like not enough people talk about it. Your lip products matter (almost) as much as your outfit. Since you’re going to be sipping on wine all day, you want a gloss, balm, or lip tint that won’t transfer like crazy. You can always reapply, but you shouldn’t constantly feel like you have to!
Go hands free with your bags.
Your hands will be occupied most of your day with snacks, drinks, and tons of picture-taking. To save yourself the stress of having to keep up with a bag every time you set it down, opt for something hands free—like crossbody bags or belt bags. I’ll link two of my favorites below!


Prioritize comfort with style so you aren’t uncomfortable.
Don’t forget that you’ll most likely be doing lots of standing, sitting, moving, and of course, drinking. Wear something that looks elegant but feels comfy. Pro tip: test your outfit out for movement before you go. Trust me, you’ll thank yourself later.
These style tips will have you looking and feeling your best for your day full of wine tasting.
There you have it! My favorite outfit to wear wine tasting, as well as some essential styling tips that can make outfit planning sooo much easier. No matter what time of year you plan to go wine tasting in, there are plenty of ways to make a statement with your look!
Thanks for reading! What’s your favorite outfit to wear wine tasting? Do you have any styling tips that you swear by? Let me know in the comments, I can’t wait to read them.
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