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I cannot emphasize this one enough! Wear cute flats or wedges.

Save your stilettos for the cocktail bar.

When you visit a winery, you may be walking outdoors checking out the soil in the vineyard as we did in Douro Valley, Portugal. Any heel is going to get stuck in that dirt.

Or you may be navigating steep steps in an ancient chalk cave in the Champagne region in France. I would have died if I was wearing heels.  

Here are my three go-to winery shoes:

The Cole Haan Anica Sandals may be the most comfortable thong sandals I have ever owned. I have the nude and rose/gold metallic sandals, which go with basically anything.

I not only wear them at wineries but for travel in general. They worked perfectly for our recent wine tours in Champagne and Burgundy, France as shown in the photo above.

I am addicted to Rothy’s Pointed Toe Flats and own too many pairs that I care to admit.

They are super comfortable and you can throw them in the washer when they get dirty. There are so many fun colors to choose from.

I also love how a pointed toe can give the appearance of longer legs.

The Rothy’s are great for visiting a winery in the spring or fall. I wore them when we visited the Central Otago wine region in New Zealand, which you can see a little bit in this photo.

I love classic staple pieces.

The Tory Burch ballet flat is one of them.

They are not as comfortable as the Rothy’s or the Cole Haan Anica sandals, but they are still very comfortable and won’t kill your feet walking through a vineyard.

The Tory Burch ballet flats are a great spring/fall winery shoe. I wore them in the Hemel-en-Aarde Valley wine region in South Africa and in the Goriska Brda wine country in Slovenia.

Great way to elevate an outfit.

You will need both hands to do all of that sipping, so you will want to be hands-free.

I strongly recommend wearing a crossbody purse. That way you can move about freely without doing a juggling act with your wine glass.  

Some of my favorites are the classic Burberry as seen in the photo above. I purchased this staple piece through Gilt, which offers great designer discounts.

Another one of my favorites that I take on our wine vacations is the Lo & Sons Pearl purse (seen in most of my photos across my body as a light grey strap).

The creator of Lo & Sons has an incredible story. I love supporting strong innovative women.  

The wine cellars can get quite cool.

Prepare by having a cardigan or light jacket ready just in case.

Cute options that I’ve worn include the Lilly Pulitzer denim jacket (surprisingly soft for a denim jacket!) or a preppy J.crew blazer.

I’ve also just worn a light cardigan like when we were in the Yarra Valley wine region in Australia as pictured above.

White House Black Market usually has some great cardigan options, which is what I’m wearing above. 

Another great layering option is the wrinkle-resistant, figure-flattering Anatomie city slick jacket.  

I’ve taken this jacket on quite a few trips including on a recent wine tour in Goriska Brda, Slovenia as shown in the photo above.

This is a fantastic layering jacket and travel jacket in general!

Feminine, flowy dresses are my favorite outfit to throw on for a visit to a winery in the spring or summer.

I love the women-led brand Amour Vert.

I am wearing one of their red numbers in the photo above, which was taken at Quinta do Tedo in Douro Valley, Portugal.

Another one of my favorite places to find cute sundresses is Revolve.

So many cute choices, almost too many.

For the fall, I love wearing Athleta’s Sculptek dark denim skinny jeans, a brightly-colored shirt and scarf, a blazer, and my Rothy’s or Tory Burch ballet flats. The picture above was taken in the Central Otago wine region in New Zealand.  

For the winter, I switch out the blazer for my long J.crew lady day coat and slip into my super comfortable Nisolo booties with a block heel.

After a few glasses of wine, you will be thankful you saved that cute romper to wear for another day.

Avoid outfits that are too fussy with a million buttons or those that take 10 minutes to take off to use the restroom.

Comfort is king.

I purchased this super comfortable black shift dress with lace trim through Lulus (pictured above), which is no longer available. However, Amazon has quite a few comparable dresses.

Some blogs will tell you it’s ok to throw those cute white jeans on if you’re not a “spiller.”

However, in my opinion, even if you are super careful, inevitability the person beside you may not be. And despite your best intentions, that lovely glass of pinot noir may find its way onto your lap.

If you do end up with a wine stain, try out some Wine Away Stain Remover. Never actually had to use it, but it’s highly rated and has been featured in Food & Wine, Today Show, Washington Post, and many others.

You will be doing a lot of tastings, so either throw on a little Aquaphor lip ointment or wear a long-wearing lipstick that’s not going to transfer.

One of my favorites is Pat McGrath’s LiquiLUST matte lipstick.

You will be doing quite a bit of sniffing. If you are doused in perfume, you will not be able to smell what you are drinking (and neither will those around you!).

Skip it and save it for dinner.  

If you go to a winery you will likely be walking around the vineyard and maybe even doing your tasting outdoors. Wear sunscreen!

I’m a little bit of a skincare diva.

Keep that skin beautiful and free of wrinkles and brown spots.

My absolute favorite is Elta MD UV Clear sunscreen.  

I love classic pieces, so my go-to sunglasses are my Ray Ban aviators as pictured above.

No squinting! I’m avoiding those crow’s feet as long as I can.

A cute hat is another great way to protect that gorgeous skin of yours while sauntering through the vineyards.

My favorite is the wide-brimmed J.crew hat.

We love checking out the wine regions in the countries we visit. From fancy estates to visiting winemakers in their garages, we have enjoyed experiencing it all.

If you are like me, I always stress about what to wear and want to make sure I dress appropriately for the occasion. I hope these tips help you as you come up with your own cute winery outfit.

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Questions about what to wear at a winery?

Let me know in the comments below!