19+ Chic Fall Winery Outfits For Your Trip To The Vineyard

Are you wondering what to wear to a winery in the fall? Get inspired with 19+ chic and modern fall winery outfits and fall wine tasting outfit ideas to recreate in 2024!

collage of four women wearing stylish fall winery outfits

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What To Wear To A Winery In The Fall

Fall is a glorious 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 many wineries have special events to celebrate the harvest. 

But are you wondering what to wear to a winery in the fall? 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. 

Read on to get inspired with chic fall winery outfits that will have you feeling stylish and confident while sipping Sauvignon and enjoying the views. 

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

get the look:

Fall Wine Tasting Outfit Ideas for 2024

When visiting a winery in fall 2024, 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.

Below are some of our favorite fall wine tasting outfit ideas and what to wear to a winery in the fall for specific months. 

Knit sweater + wide leg pants.

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

get the look:

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.

Mini skirt + bell-sleeve top.

a woman wearing a taupe mini skirt, a black bell sleeve top, and tall black boots

get the look:

You can definitely get away with a mini skirt in early fall or if you live somewhere that stays throughout autumn.

This taupe mini has serious fall vibes, and the black bell-sleeved blouse adds a sleek and feminine touch that upgrades the whole look. Finish the outfit with tall boots, a simple handbag, and a statement belt.

If you do want to add another layer, sheer black tights or nude-toned stockings will pair well with this ensemble. 

Denim midi skirt + a long coat.

a woman wearing a denim midi skirt with a black sweater, a black and white plaid long coat, and black leather boots

get the look:

A denim midi skirt is a chic and trendy cool-weather piece perfect for a day of strolling through a winery. A classic black sweater and tall leather boots will keep you warm throughout the day, while the long coat adds an extra layer when needed.

The plaid print adds visual interest here, while the neutral tones keep the outfit effortless and elevated. However, you can add color with rich jewel tones or warm shades of brown.

Denim jacket + chelsea boots.

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

get the look:

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.

get the look:

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.

get the look:

A midi dress is a perfect fall wine tasting outfit 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.

get the look:

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 should I wear to a wine tasting in October?

October is one of the best months for a wine tasting as the weather is cool but not chilly, so it’s perfect for spending time outdoors at a winery. If you’re going to a wine tasting in this month, you’ll want to dress appropriately for the cooler temperatures.

Below, we’ve listed some of the best pieces to wear for a winery outfit in October:

  • Knit sweater
  • Long-sleeved tee
  • Denim jacket
  • Blazer
  • Jeans
  • Midi skirt or dress
  • Pleated trousers or palazzo pants
  • Loafers
  • Low heels
  • Ballet flats
  • Chelsea boots or tall boots
woman wearing a black cropped jacket with a black top and off-white jeans with black low pumps at a winery in the fall

get the look:

What do you wear to a winery in November?

November is a great time to go to a wine tasting, but the weather in this month is a little more unpredictable than early fall months. You’ll want to plan ahead and make sure to bring extra layers in case it gets too cold. These are some of the pieces we recommend you wear during a winery visit in November:

  • Sweater dress
  • Chunky knit sweater
  • Turtleneck
  • Long wool coat or trench coat
  • Wool blazer
  • Leather jacket
  • Jeans
  • Leather pants
  • Ankle boots
  • Tall or knee-high boots

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.

get the look:

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 fall wine tasting 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.

get the look:

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.

Wool coat, midi skirt, & ankle boots.

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

get the look:

Go for a chic and feminine fall outfit with a slip skirt and a long wool coat. A midi-length skirt is great for protecting you from any wind chill, and the ankle boots are also perfect for cold weather while adding a stylish touch to the look. 

A long wool coat is a must for autumn days, and you can wear a long-sleeved tee or fine-knit sweater underneath so that you can stay warm even if you take your coat off. We love the animal print skirt here for a bold and playful fall look, although you can never go wrong with warm, neutral tones for a fall winery outfit. 

Black sweater, trousers, + flats.

Woman wearing black trousers and a black sweater.

get the look:

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.

Wool blazer + tall  lug boots.

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

get the look:

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.

woman wearing a green jacket with jeans at a winery in the fall

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

If you happen to visit a winery on an extra cold fall or winter day, you should definitely have the right pieces and enough layers to make sure that you stay warm and cozy the whole time. We have some of the best pieces to wear for chilly days listed below:

  • Fitted sweater
  • Long-sleeved tee
  • Knit turtleneck
  • Wool or twill blazer
  • Straight-leg or skinny jeans
  • Wool pants
  • Leather pants
  • Long coat
  • Quilted jacket
  • Leather jacket
  • Sweater dress
  • Chelsea boots
  • Tall or knee-high boots

You may get lucky and have warmer weather during your wine tasting, but you’re more likely to experience colder weather, so it’s best to be prepared. Below are some of our favorite looks for cold fall or early winter winery outfits!

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 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. 

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. 

two women at a winery in the fall wearing long coats over sweaters and midi skirts with boots

Final Notes

The key for putting together the perfect outfit to wear to a winery in the fall 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.

a group of four women at a winery in the fall wearing jeans, boots, loafers, and long camel coats

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.

We hope you have been inspired with these ideas for what to wear to a winery in the fall! So, which was your favorite 2024 fall wine tasting outfit?


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