What to Wear to a Wine Tasting

Yes, I actually got that question from a reader! I’ve never been to Napa, but we do have some wineries here in Pennsylvania, and I actually went to a wine tasting last weekend. I wore something like this.

Eileen Fisher dress (S) // Vince Camuto wedges (8) // rattan earrings // layer necklace // Victoria Emerson bracelet c/o // Michele Apple Watch Band // rag & bone sunnies // Tory Burch handbag

I’m sure the dress code varies from place to place, but around here, wineries are pretty casual. I still like to wear something that looks intentional and put together, and a casual dress like this Eileen Fisher stretch cotton tank dress is perfect.

It’s comfortable and moves with you if you need to do a bit of walking, and for sitting or standing during the actual wine tasting.

And of course, this dress will work for many other purposes as well. I’ve worn it with flat sandals to church, with these wedges to go out to eat with the family, and I would even wear it with sneakers for running errands around town.

For size reference, this dress runs large, as most Eileen Fisher dresses do. I ordered the small and XS to try and I ended up keeping the XS.

These wedge sandals are casual and cute, and they’re also surprisingly comfortable. They run true to size, or size up if in between. You can find them at Macy’s, Nordstrom, and Evereve.

They would have been fine for the winery we visited last weekend, but I’ve been told by those who have been to Napa and the larger wineries that it’s best to wear closed toe shoes. There can be a lot of gravel or grass, or even a walk through the actual vineyard, so practical generally outweighs the cuteness factor.

I wasn’t really thinking in those terms when we shot this look, but you could easily swap out these wedges for a white fashion sneaker or maybe a leather espadrille. I actually had that shoe in white for a few years, and it’s very comfortable.

Being intentional with your accessories is the key to making a simple black dress like this one look appropriate for your venue.

For a wine tasting, I love these oversized rattan earrings. They bring a natural element into the look, and they’re summery and casual and fun. I also added a layered necklace since the neckline of the dress is so plain.

And this Victoria Emerson boho cuff is the perfect complement to the entire look. I love the summery, boho chic style, and the colors tie in perfectly with the shoes and earrings.

You should be able to use the code 50JoLynne for 50% off full price styles at Victoria Emerson for the month of June, but it doesn’t seem to be working at the moment. I’ve got an email out to them, so we can get it sorted out.

Layers are always a good idea for a winery because it can often be chilly inside. They’re usually stone buildings, or at least they are around here.

A denim jacket is always my first choice for a layer over a casual summer dress. I like how it offers some structure, which is far more flattering than a slouchy cardigan, and denim has that casual-chic vibe that I love.

This is the KUT from the Kloth Helena, which has been around for years. It’s a good classic denim jacket in a medium indigo wash, and it runs true to size. I have it in the small.

And don’t forget your sunglasses! Not only do they add another element of interest to the outfit, they can be very necessary if you’re outside in the afternoon.

I carried a Tory Burch leather shoulder bag because I like how it coordinates with the shoes and earrings, but a straw tote like this one would look even better with this outfit.

I’ve been meaning to add a straw tote to my summer handbag collection, but I haven’t found the right one quite yet.

While I wrote this post with a visit to a winery in mind, you could wear it almost anywhere in the summertime with a few simple tweaks.

And all of these pieces are ones you can mix and match with other items in your closet for a variety of purposes. They’re also classics you can keep for years, so the cost per wear should work out to be quite low over time.

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photos: Alison Cornell

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19 thoughts on “What to Wear to a Wine Tasting

  1. Perfect LBD and it looks great on you! I was surprised to read that Pennsylvania grew wine grapes! I just read you micro – post about white sneakers and oh Jo Lynne, I’m now thoroughly confused about which white sneaks to keep and use for travel and life. I thought the P448s were the winner, but now I’m seeing solid white sneakers everywhere like the ones you feature and wonder if I should order those to try. I’ve tried Vejas because I live the look in others, but they weren’t comfortable to me. But you have some others in your list that look cute! What would YOU choose if you had to take one pair for both denim and skirts? (The P448s are so comfortable but I haven’t worn them out of the house yet and they do have the logo writing on the side and the tan colored tongue. But I liked them with different outfits. I don’t know what to do and need a fashion stylist to advise me please! 😊)

    1. I think the P448s you showed in the FB group are adorable and perfect with all of those outfits. If you love them and they’re comfy, I’d keep them. I actually meant to include them in my roundup.

      1. Thanks for the feedback. I’m going to order one more pair of white sneaks to try and do a side by side comparison with the same outfits. My husband thinks I’m crazy 😜

  2. We have some wonderful wineries here in Bucks County where I am. I like that you can do “wine flights” now at them. I love the black dress on you with your accessories!

  3. Hey Jolene! Great post! Where did you find that Apple watch band? I LOVE it and have been looking for one similar but can’t find just the right one.

  4. Sorry! I found it in another post. I am a little behind. Love it but will need to look for something a little more affordable but it looks great on your watch!

  5. I love wearing my rattan earrings like you have, as well as the teardrop shaped ones because they are so lightweight and they add that perfect vibe to so many outfits. I’m looking to add a handbag to my summer collection and I haven’t found the one that I know is it. I have two VE bracelets enroute now, and due to the number that I have, I need to forget that we have a 50% off code this month, through you.

    1. I’m giggling while while reading this and watching my daughter at gymnastics. I read “50% off VE code” and immediately starting reviewing my mental wish list! But I have sooooo many wonderful VE bracelets, and my sister in law just gifted me 2 more for my birthday! 🤣🙈

  6. We have 40 wineries in Loudoun County, which is in Northern VA, so going to wineries is a regular pastime, especially now that my boys are teenagers. In fact, we’re wine club members at Cooper’s Hawk so we go once a month for the free tastings. I always level up for Cooper’s Hawk since it’s indoors (and a restaurant) and wear a nice top, jeans and a heel or wedge sandals. We often sit at the bar and eat appetizers after a tasting, so another reason to dress up. When we go to a winery out in the countryside, I wear similar but might wear flats depending on terrain. Most people in this area look nice at wineries, above grocery shopping outfits. The younger women tend to wear dresses in summer, and I do sometimes, but usually I wear nice shorts and cute top.

  7. Living way down south, I don’t really think there are any wineries near us. But we do have a rum distillery that offers tours and we love to do that! The actual distillery is not air conditioned 🥵 but the attached restaurant is. So I like the idea of layers!

  8. Really like the look of those Veja sneakers, must be a good one because Northstrom only had a size 5 left. I have a Northstrom gift certficate burning a hole in my pocket. I have a pair of Ugg white sneakers that I love, think Cindy Spivey turned me on to them 3-4 years ago and would love these to change up. Maybe they’ll be back in stock again soon. Thanks for all your great ideas!

      1. Thanks, they really caught my eye with your outfit from the Disneyland park post. This type shoe is my go to with t-shirt dresses and oh so many others!

  9. I’m currently in Vermont on a brewery tasting trip. I wore a black dress with my jean jacket yesterday to Hill Farmstead, I wore my birks and just had to be careful on the loose gravel. The outfit was perfect for dinner at a cute bistro around the corner for us. Today I’ll swap a different dress in but stick with the Birks for HFS and maybe throw my wedges in the car for when we head to Burlington tonight. Breweries are way more laid back. I wore jeans, a T and black track jacket/sneaks on Wednesday. I left my white sneaks at home because it’s still mud season in Vermont.

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