14+ Modern Fall Winery Outfits For Your Next Trip To The Vineyard

Fall is a beautiful time of year, and what better way to enjoy it than by visiting a winery? Look no further if you’re looking for some inspiration with 14+ chic and modern fall winery outfits to copy! 

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Woman wearing an animal print midi skirt, tan sweater, black booties and a black coat.

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What To Wear To A Winery In The Fall

Fall is the perfect time to visit a winery. The weather can still be slightly warm, and the changing leaves create a truly beautiful setting. It’s also harvest season and lots of wineries have special events to celebrate the harvest. 

But what should you wear for your winery visit? You will find that most wineries do not have a specific dress code which gives you a chance to really have fun when putting together outfits. 

Woman wearing jeans, a black sweater and a black coat.

get the look:

Fall Wine Tasting Outfits 2022

When visiting a winery in the fall, here are some things to keep in mind:

  • Consider the type of winery you’ll be visiting. If it’s a casual winery, jeans and a sweater will suffice. However, if it’s a more upscale winery, you’ll want to dress up a bit more. A nice blouse or dress is always appropriate.
  • Consider the activity you’ll be doing at the winery. If you’re planning on doing a lot of walking, comfortable shoes are a must. Loafers, boots, or flats are acceptable, but avoid anything with very high heels as you’ll be spending a lot of time on your feet.
  • Don’t forget to bring along a jacket or scarf. The temperature can drop quickly in the fall, so it’s always good to be prepared.

What should I wear to a wine tasting in October?

October is the perfect month for a wine tasting. The weather is cool but not too cold, making it comfortable to spend time outdoors. Opt for knit sweaters, jeans, trousers, boots, and lightweight jackets

If the weather is still warm enough, you can go with a midi dress or slip skirt, paired with sandals, boots, or flats. Always bring an extra layer in case the air has more of a chill.

Below are some of our fall winery outfits to copy! 

Knit sweater + wide leg pants.

Woman wearing black, wide leg pants and a cream sweater.

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A cozy sweater and wide-leg pants are perfect for a wine tasting in September or October. Because the weather in the fall can be so unpredictable, the sweater can be easily layered over a long sleeve shirt or t-shirt for extra warmth.

For warmer fall days, you can layer a silk cami under the sweater that can be worn on its own with wide-leg pants. This look always looks great with flat sandals or mules on warmer fall days.

Denim jacket + chelsea boots.

Woman wearing black jeans, brown booties, a white sweater and a denim jacket.

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Is a denim jacket suitable for a winery? Sure! But, one that is more laid-back and casual. This look with black skinny jeans and a jean jacket is a classic combination. 

The jeans are versatile and can be dressed up or down, while the denim jacket is a perfect layering piece for cooler weather. The outfit is elevated by a pair of heeled suede chelsea boots, but you could also wear loafers if you want flat shoes. 

For added warmth, pack a blanket scarf that will keep you warm as the sun starts to go down.

Camel sweater + neutral trousers. 

Woman wearing white trousers an a tan, knit tip.

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Who says you can’t wear white after Labour Day? Camel and creamy neutrals are always a chic choice for spending a fall day at the vineyards. In addition to being trendy, the look is very polished.

This outfit can be styled for warmer weather by adding brighter colors in accessories or swapping the sweater for a tank top. For cooler weather, add a scarf or wool blazer.

Long-sleeve midi dress + sandals.

Woman wearing a black and white patterned middi dress and sandals.

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A midi dress is a perfect outfit for a wine tasting in September or early October because it is comfortable, elegant, and easy to style for both warmer fall days and cool nights. 

A long sleeve midi dress is perfect for autumn weather as it will keep you warm while still looking very polished. This dress can be styled for warmer weather by pairing it with sandals. Or, add a pair of tights, booties, and a jacket for cooler weather.

Slip skirt + bodysuit.

Woman wearing a black midi dress and sandals.

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This is an excellent outfit option for visiting a winery in the early to mid-fall when the weather is still warm. You can never go wrong with a black slip skirt, which is always a classic choice for any occasion. 

A midi slip skirt will always make you look polished and chic.You can style this outfit for colder fall weather by adding tights and boots, and swapping the tank bodysuit for a long sleeve bodysuit. 

What do you wear to a winery in November?

The weather in November can be very unpredictable so you’ll need to dress accordingly. There may be days where the weather is warm enough to wear a sweater dress and other days you’ll need to layer with a warm coat. Boots are always the best choice for footwear, along with knit sweaters, and layering pieces like a wool blazer or leather jacket.  

Check out our favorite November winery outfits below, and see this list of wine tasting outfits from Whimsy Soul!

Trench coat + ankle boots.

Woman wearing black jeans, black boots, a grey sweater and a tan trench coat.

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A trench coat and ankle boots are two of the best fall accessories. This outfit is perfect for a winery in November because it is comfortable and stylish. The trench coat is a classic piece that will keep you warm, while the booties add a touch of style. 

This outfit can be styled for warmer weather by removing the trench coat or wearing a light jacket or sweater. For cooler days, wear a turtleneck, a scarf, and a wool fedora hat to finish the look.

Oversized knit sweater + pants.

Woman wearing black pants and a black and tan turtleneck sweater.

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An oversized sweater is perfect to wear to a winery in November. It is cozy and chic and can be styled in many different ways.

For warmer fall days, swap the ankle pants for a skirt. You can wear this look with booties or even over-the-knee boots.

For cooler weather, swap out the pants for leggings and knee-high boots. And, for those snowy November days, you can throw on a wool coat for a warm, cozy, and chic look.

Black sweater, trousers, + flats.

Woman wearing black trousers and a black sweater.

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All black is the perfect way to go for a chilly day at the winery. Start with an cozy sweater and wide-leg pants. A pair of two-tone flats ties in the look nicely on a warmer fall day. 

However, if you’ll be experiencing cooler weather, add a black wool coat and swap out the flats for ankle boots to finish the look.

Leather midi skirt + knee-high boots.

Woman wearing a leather skirt, black boots and a white turtleneck sweater.

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A brown leather skirt is a perfect addition to your fall closet. For a day at the winery, add a cream-colored turtleneck and finish the look with knee-high boots.

When the weather is warmer, you can wear a skirt with a short sleeve shirt or a silk cami. And for cooler weather, add tights and a long wool coat which will give you extra warmth while still looking chic and put together.

Wool blazer + tall  lug boots.

Woman wearing black leggings, black riding boots, a brown blazer coat and a brown sweater.

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A wool blazer and tall boots are perfect for a winery in November. The jacket will keep you warm and makes for a great layering piece. On warmer days, remove the jacket or swap it out for a lighter version. On cooler days, add a wool fedora in a matching neutral color.

The tall boots pull the whole outfit together and give a very equestrian look. You can also swap out the boots for ankle booties and still look classy.

What do you wear to a winery when it’s cold?

For a winery in the later fall and early winter months, you’ll want to ensure you’re prepared for the cold weather. Layering with a wool coat and heavy knit sweater is a good idea. Choose long pants and ankle boots or tall boots.

While there is still a chance to have warm sunny days, cooler weather is more likely during this time of year. Below are our favorite looks for winery visits in colder weather.

Cozy knit sweater set.

Woman wearing a knit midi skirt and a tan sweater.

get the look:

A cozy sweater set or sweater dress is perfect for a cold winter day at a winery. If you’ll be inside most of the time, you can wear a pair of stylish pumps like the photo above. But, if you’ll be outdoors too, go with a pair of knee high boots. 

When the temperatures really drop, layer the dress with a camel wool coat for a monochromatic look. And, don’t forget to wear tights to keep your legs warmer. 

Herringbone wool coat + pants.

Woman wearing black cigarette pants and a tweed coat.

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Herringbone is very stylish and makes for the perfect piece on a cool November day at the wineries. The herringbone wool jacket is warm and will keep you comfortable.

At the same time, the ankle-length pants and loafers provide a sophisticated look. For cooler weather, swap out the pants for full-length leggings or skinny jeans and add a pair of booties or over-the-knee boots for additional warmth.

Over-the-knee boots + wool jacket.

Woman wearing skinny jeans, over the knee boots, a tan sweater and a black blazer coat.

get the look:

Over-the-knee boots are a perfect addition to the fall winery outfits list. They keep your legs warm and look great with a pair of jeans and a neutral sweater.

Add a wool coat or blazer for a more polished look (and extra warmth). You can also wear this outfit on a warmer day by swapping the jeans for a suede mini skirt and removing the blazer. 

What do you wear to a fall winery?

The key is putting together the perfect outfit to wear to a fall winery is layering.Start with a basic outfit such as a pair of jeans, sweater, and booties, and get creative with accessories such as hats and scarves. You can dress up this look by swapping the jeans for a skirt on warmer fall days.

Additionally, you can dress your outfit down and go more casual with a pair of loafers or flats. The most important thing is to be comfortable and ready for whatever the fall weather has in mind so you can spend more time sipping on wine and enjoying the views.

What is your favorite fall winery look?


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