What to Wear to a Winery in the Fall

Free People Getaway Midi Dress, King Family Vineyard | What to Wear to a Winery by popular D.C. fashion blogger, Alicia Tenise: image of Alicia Tenise standing outside at at winery and wearing a Free People Getaway Midi Dress and Lack of Color Benson Tri hat.

If you’re new here, you know that I like wine. Like, a lot. And not only that, but I’m a certified wine enthusiast as well. 

I love going to wineries right now in particular because depending on where you go, you can easily make this a socially distanced activity. Some of the wineries in Charlottesville have huge plots of land where you can easily spread out and not come within 20 feet of another person. Also, October is Virginia Wine Month, so it’s definitely a great time to plan a trip to wine country!

I’ve been to almost 100 wineries in my life, and I’ve worn some amazing pieces while wine tasting. But, I’ve also worn totally impractical things as well. Today, I’m sharing some tips and tricks on what to wear to a winery!

Karen Walker Number One Sunglasses, Lack of Color Benson Tri - Black | What to Wear to a Winery by popular D.C. fashion blogger, Alicia Tenise: image of Alicia Tenise standing outside at at winery and wearing a Free People Getaway Midi Dress and Lack of Color Benson Tri hat.

Flat Boots Are Your Friend

You’re going to be doing a lot of walking outdoors when you go to wineries. You’ll likely find yourself walking on gravel, dirt roads, uneven fields, heck, maybe you might even have to walk up a mountain.

I’d recommend leaving the heels at home. Heck, even a kitten heel will drive you crazy at a vineyard! I love wearing my Yale Boot underneath my dresses — I bought this right before my California road trip last year, and they’ve held up well. They’re super comfortable, sleek, and I can walk for miles in these shoes!

Stick to Flowy Fabrics

A skintight sweater dress in the fall might sound good in theory, but it’s not the most practical outfit option. For one, you’re likely going to be sitting either at a picnic table or on the ground when you visit a winery, so you want something that you can easily stand up/sit down in. A flowy maxi or midi dress has always been a solid bet for me because it’s stylish yet ideal for any situation!

Layer Up

Depending on where you might be going wine tasting, it might be a good idea to bring some layers. The higher the elevation the winery is, the colder the temps will be. It might feel pretty warm in the valley, but once you head up a mountain, it might get a bit brisk!

Avoid Mini Skirts/Dresses

I usually only wear a mini skirt/dress to a winery if I have a reservation, and I know I’m going to be sitting at a table. If I don’t, I avoid them. Why? Standing up/sitting down at picnic tables, lawn chairs, or on the ground is a bit awkward, and you might not be the most graceful while doing so (especially after a glass or two of vino!)

Wear Something You Can Spill On

So, there’s a slight chance that you might spill red wine on your outfit during a winery outing. As much as I love my tide-to-go pen, it doesn’t make sense to wear an all-white ensemble while wine tasting! I love wearing prints because if you get a tiny spill on your outfit, you won’t freak out!

See More of my Favorite Winery Outfits:

Post One | Post Two | Post Three

Photos by Tom McGovern

Do you have any extra tips on what to wear to a winery?  Let me know in a comment below!

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