The 7+ Cutest Winery Outfit Ideas For Your Next Wine Tasting

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I love going to a winery. Whether it be in the Hamptons, Napa, or a local winery, there is no better place to be to enjoy a glass of wine. It is a great first date idea or a place to go with friends. Either way, you want to look chic, but not over the top. It is a vineyard after all. There is plenty to do at a vineyard for the day. Whether you are a wine connoisseur or not, there are tours, music and food at the vineyard. Whether you’re on a date, or simply enjoying a girls day at the Hamptons, there are plenty of chic and easy winery outfit ideas for your next trip.

What To Wear To A Winery?

There are a few things to consider when you plan your next trip to the winery. People plan to go to the winery throughout the year and different seasons. The most popular season is Summer, followed by the Fall season. The Summer season is popular for music festivals ,weddings, or work events at a vineyard. During the hot, Summer season it is important to wear lightweight clothing and sandals. It can get very humid at vineyards during July and August. A midi dress is the most popular winery outfit idea for the Summer. A midi dress is the perfect casual, yet dressy piece for the vineyard. Pairing a midi dress with sandals or sneakers can be the best footwear option.

For the Fall season, I would bring along a sweater or light jacket. Also, switching the midi dress for a sweater dress would be an appropriate option. Jeans is also an option for the Fall when visiting a vineyard. Cowboy boots can be worn to have a trendy look.

The below is more appropriate for the Summer months, since that is the more popular time to visit wineries. From midi dresses to cowboy boots outfits, there are plenty of winery outfit ideas to enjoy a glass of wine.

Scroll below for 9+ winery outfit ideas for the Summer or Fall.

What To Wear To A Winery In The Summer

1. Floral Midi Dress + White Sneakers + Fedora Hat

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Instagram @amorrelll

Comfortable Shoes

Wearing comfortable shoes, whether it be sneakers or flat sandals is an important point. I know you feel like you need to whip out your high heel shoes, but it is so impractical to walk around in vineyards with heels.

You should only consider heels when you know you will be sitting down for a tasting and not walking around. I recommend sandals, flat loafers, or white sneakers for a day at the vineayard. Also a side note, white sneakers are so chic and white sneakers and dresses have been trending.

2. White Strap Dress

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Instagram @jjaneslee

Midi/Maxi Dresses

A white or patterned dress is the classic winery outfit. The ensemble is a perfect laid back, yet chic outfit. It is perfect with sneakers or flat sandals. It is also perfect for the Summer months – the lightweight material works well with the humid, dry air.

A pretty midi dress is the perfect balance between casual and dressy. Therefore, it can be the perfect wine tasting outfit and also be comfortable enough for a tour around the vineyard.

If you think wearing a white dress is a little dull, brighten up the look with some small accessories to decorate the dresses.

While it is important to wear the right clothes and bag to a winery, it also also great to have a unique look that complements your style.

An easy way to have the style you like, is to customize your look to your own aesthetic. A unique way is through custom patches! Patches can be added to a denim jacket to make it your own.

3. Floral Maxi Dress + Basket Bag

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Instagram @bylaura.ann

Basket Bags

During a vineyard trip, it’s important to have a fuss-free bag. A bag that says Summer time is the basket bag. A bulky bag is not convenient for a trip to the vineyard. You don’t want to walking around the vineyard with a giant bag.

Also, a basket bag is the perfect bag if you are worried about spilling wine. It is such an easy bag to clean and doesn’t stain like a leather bag. Basket bags are the perfect accessory for any outfit for a trip to the vineyard.

4. Blue Cut Out Dress + White Sandals

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Instagram @camrynmoss

4. Black Crop Top + Linen Pants + Black Sandals

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Instagram @topwineries

Linen Pants

Linen clothing is a great option for a Summer visit to the winery. There are plenty of winery outfit ideas that you can wear with linen pants.

Linen pants are so versatile. They can be paired with any color top or even with a linen top.

It is important to wear lightweight clothing, whether it is linen pants or a maxi dress, at a vineyard. Linen pants are the perfect neutral pants that can be styled with lots of different options.

5. Bardot Top + Linen Pants + White Strappy Sandals

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Instagram @bynicolemaddie

6. Linen Tank Top + Linen Pants + Brown Sandals

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Instagram @bordeaux.blonde

What To Wear To A Winery In The Fall

7. Long Sleeve Floral Dress + Black Cowboy Boots

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Instagram @buddylovesrachel

Cowboy Boots

Cowboy boots are the perfect way to make any outfit Fall ready. They are the perfect footwear for a winery in the Fall season.

Cowboy boots look great with a long sleeve dress, jeans, or a romper. They are great to walk around a wet vineyard without ruining a pair of sneakers or loafers.

Floral Maxi Dress + Brown Cowboy Boots

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Instagram @buddylovesrachel

Floral Maxi Dress

I would argue that floral dresses are more suited for the Fall than any other season. Long sleeve floral dresses are perfect for the cooler weather, but still chic enough for a trip to the vineyard.

Floral maxi dresses are also a stylish option for a Fall wedding or engagement at a winery. It is one of the most versatile dresses in a women’s wardrobe.

Fedora Hat + Sweater Dress + Boots

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Instagram @ashhxcruz_

Sweater Dress

If I would be visiting a winery in the Fall, I would choose a sweater dress. They are incredible chic, yet relaxed enough to spend a day at a vineyard.

With the change of temperatures in the Fall, a sweater dress is the perfect dress for the chilly conditions. Wear with boots, cowboy boots, or sneakers. I would also bring a light jacket or denim jacket for the cooler weather.

Blazer + Jeans + Mules

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Instagram @casey_mcadam

Jeans

There is a large debate whether jeans are winery appropriate. I would argue that jeans are perfect for the Fall season.

I would style jeans with blazers or a nice top. Blazers are the perfect stylish look with jeans. Wear with loafers or boots to complete the look. Whatever you choose, I am sure that you will look great for your next trip to the vineyard.