19+ Stunning Winery Fits for Fall Vineyard Trips 2025

Struggling with fall winery attire? Discover 19+ stylish and contemporary fall winery outfits and fall wine tasting outfit ideas to inspire your 2025 wardrobe!

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What To Wear To A Winery In The Fall

Autumn is the perfect season for winery visits! Expect pleasant, mild weather. The vibrant fall foliage provides a stunning backdrop. Plus, it’s harvest time! Many wineries host unique events to commemorate the grape harvest.

Struggling with fall winery outfit ideas? Relax! Most wineries don’t enforce a strict dress code. This allows for creative and enjoyable outfit choices.

Discover stylish fall winery outfits for 2025! Feel confident and chic while enjoying Sauvignon and breathtaking views. Get inspired now!

Woman wearing jeans, a black sweater and a black coat. — @anoukyve

get the look:

Fall Wine Tasting Outfit Ideas for 2024

Planning a winery visit in autumn 2025? Here’s what you should consider:

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.

Discover our top fall wine tasting outfit suggestions! Get inspired on what to wear to a winery during the autumn months. We’ve curated ideas for specific months to help you choose the perfect look.

Knit sweater + wide leg pants.

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

get the look:

Enjoy wine tasting this autumn in a comfortable sweater and wide-leg pants. September and October weather can be changeable, so layer your sweater over a long-sleeve shirt or tee for added warmth. This ensures you’re prepared for any temperature shift.

Enjoy mild autumn days by layering a silk camisole beneath your sweater. The cami can also be worn solo with wide-leg trousers. This ensemble pairs perfectly with flat sandals or mules when the weather is warmer.

Mini skirt + bell-sleeve top.

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

Achieve the Style:

Mini skirts remain stylish in early fall, especially in warmer climates. They’re a great transitional piece for your wardrobe.

This taupe mini skirt is perfect for autumn. The black bell-sleeved blouse adds a sophisticated, feminine touch, elevating the entire ensemble. Complete the look with tall boots, a minimalist handbag, and a bold statement belt.

Want to add a touch more? Sheer black tights or nude stockings complement this outfit beautifully.

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 — @jasmine_makai

Achieve the Style:

A denim midi skirt offers a stylish and modern look, ideal for a winery visit during cooler months. Pair it with a timeless black sweater and tall leather boots for warmth. Add a long coat for extra protection against the elements.

Plaid offers a stylish visual element. Neutral colors ensure an easy, sophisticated look. Enhance it with vibrant jewel tones or cozy browns.

Denim jacket + chelsea boots.

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

get the look:

Can you wear a denim jacket to a winery? Absolutely! Opt for a relaxed, casual style. A denim jacket paired with black skinny jeans is a timeless and stylish choice.

Jeans offer incredible flexibility, easily transitioning from casual to chic. A denim jacket provides ideal layering for brisk days. Suede heeled Chelsea boots enhance the ensemble, though loafers provide a comfortable, flat alternative.

Stay cozy as evening approaches! Bring a blanket scarf for extra warmth when the sun dips low.

Camel sweater + neutral trousers.

Woman wearing white trousers an a tan, knit tip. — @cocobassey

get the look:

Forget the old “no white after Labor Day” rule! Camel and soft neutrals remain stylish for autumn vineyard visits. This look is both fashionable and sophisticated.

Adapt this look for summer by incorporating vibrant accessories or a breezy tank top instead of the sweater. When temperatures drop, layer with a cozy scarf or a stylish wool blazer.

Long-sleeve midi dress + sandals.

Woman wearing a black and white patterned middi dress and sandals. — @daphnemoreau

get the look:

For September and early October wine tastings, a midi dress is ideal. It offers comfort, sophistication, and effortless styling for both warm autumn afternoons and chilly evenings.

The long-sleeve midi dress is a fall fashion essential. It offers warmth and a sophisticated look. Adapt this versatile piece for warmer days with sandals. When temperatures drop, simply add tights, ankle boots, and a stylish jacket.

Slip skirt + bodysuit.

Woman wearing a black midi dress and sandals. — @thenickienicole

get the look:

Looking for the perfect winery outfit this fall? This ensemble is ideal for those warm, early to mid-autumn days. A black slip skirt is a timeless and versatile piece that always makes a stylish statement.

A midi slip skirt guarantees a refined and stylish appearance. Adapt this ensemble for cooler autumn days by incorporating tights and boots. Replace the tank bodysuit with a long-sleeved version for added warmth and comfort.

What should I wear to a wine tasting in October?

October remains a prime month for wine tasting in 2025. The weather is comfortably cool, ideal for outdoor winery visits. When attending a wine tasting this October, dress suitably for the mild temperatures.

Here are some top outfit choices for a winery visit 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 — @sevenaugust

Achieve the Style:

What do you wear to a winery in November?

November 2025 offers fantastic wine tasting opportunities! However, the weather can be quite changeable. Planning ahead is key. Pack extra layers to stay comfortable if temperatures drop. Here are our top clothing recommendations for a winery visit this 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

Explore our top winery outfit picks for November. Also, discover more wine tasting outfit ideas courtesy of Whimsy Soul!

Trench coat + ankle boots.

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

get the look:

A trench coat paired with ankle boots remains a top fall fashion choice in 2025. This ensemble offers both comfort and style, making it ideal for a November winery visit. The timeless trench coat provides warmth, while the ankle boots inject a fashionable edge.

Adapt this autumn wine tasting ensemble for warmer days. Simply ditch the trench coat or opt for a light jacket or sweater. When the temperature drops, add a turtleneck, scarf, and a stylish wool fedora to complete your look.

Oversized knit sweater + pants.

Woman wearing black pants and a black and tan turtleneck sweater. — @cocobeautea

get the look:

An oversized sweater is ideal for a November winery visit. It’s both comfortable and stylish, offering versatile styling options. On warmer autumn days, replace ankle pants with a skirt. Complete this outfit with booties or even thigh-high boots.

As temperatures drop, trade your pants for leggings paired with stylish knee-high boots. When November brings snow, add a wool coat for a warm, comfortable, and effortlessly chic ensemble.

Wool coat, midi skirt, & ankle boots.

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

Achieve the Style:

Craft a stylish and feminine autumn ensemble with a slip skirt and a long wool coat. A midi skirt offers excellent protection from chilly winds. Ankle boots are ideal for colder weather, enhancing the look with a fashionable flair.

A wool coat is essential for crisp autumn days. Layer it over a long-sleeved tee or a lightweight sweater for adaptable warmth. This animal print skirt adds a fun, daring touch to your fall style. Alternatively, classic neutral colors are always a perfect choice for a winery visit in the fall.

Black sweater, trousers, + flats.

Woman wearing black trousers and a black sweater. — @fakerstrom

get the look:

An all-black outfit is ideal for a cool winery visit. Begin with a comfortable sweater and flowing wide-leg pants. Two-tone flats complete the ensemble beautifully, perfect for a mild autumn day.

For colder days, enhance your style with a black wool coat. Replace flats with ankle boots for a polished, weather-appropriate finish.

Wool blazer + tall lug boots.

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

get the look:

Visiting a winery in November? A wool blazer paired with tall boots is an excellent choice. The blazer provides warmth and is ideal for layering. If the weather is mild, simply remove the blazer or opt for a lighter jacket. For colder days, consider adding a stylish wool fedora in a complementary neutral shade.

Tall boots complete the ensemble, creating a chic, equestrian-inspired style. Alternatively, ankle booties offer a similarly sophisticated touch.

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

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

Visiting a winery on a cold autumn or winter day? Ensure you’re warm and comfortable with the right clothing. We’ve curated a list of ideal pieces for those chilly winery visits:

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

Wine tasting can be unpredictable! While you might catch a warm day, cooler weather is more common, especially in fall or early winter. It’s wise to plan ahead. Here are some top outfit ideas for chilly winery visits!

Cozy knit sweater set.

Woman wearing a knit midi skirt and a tan sweater. — @beatrice.gutu

get the look:

Embrace a chilly winery visit with a comfortable sweater set or dress. For indoor settings, chic pumps are ideal, as seen in the image. If venturing outside, opt for knee-high boots instead.

As temperatures plummet, create a chic, monochromatic style by layering the dress with a camel wool coat. Remember to wear tights for extra warmth on your legs.

Over-the-knee boots + wool jacket.

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

get the look:

Elevate your winery style this fall with over-the-knee boots. They offer warmth and effortlessly complement jeans and a cozy, neutral sweater.

Elevate your style with a wool coat or blazer for a refined appearance. (Plus, added warmth!) Adapt this ensemble for warmer weather. Simply switch jeans for a suede mini skirt and lose the blazer.

two women at a winery in the fall wearing long coats over sweaters and midi skirts with boots — @eta.alaniz

Final Notes

Layering is essential for crafting the ideal winery outfit this autumn. Begin with a simple base: jeans, a cozy sweater, and stylish booties. Then, personalize your look with fun accessories like hats and scarves. For warmer fall days, elevate the ensemble by replacing jeans with a chic skirt.

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

For a more relaxed vibe, consider pairing your ensemble with loafers or flats. Prioritize comfort and preparedness for unpredictable autumn weather. This way, you can fully immerse yourself in wine tasting and scenic beauty.

Hopefully, these autumn winery outfit ideas have sparked your imagination! Which 2025 fall wine tasting ensemble is your absolute favorite?