Sipping wine surrounded by the beautiful colors of fall is a perfect way to spend an afternoon.
When planning your winery visit, putting together the right outfit is key.
You’ll want to look stylish yet comfortable as you walk around tasting wines.
The good news is fall fashion lends itself perfectly to winery attire.
Rich hues, cozy knits, and chic layers make putting together winery looks effortless.
Now you’ll find chic, seasonal looks ranging from casual to dressy.
We’ll provide in-depth details on each piece so you can recreate these stylish ensembles.
Distressed Jeans and Flannel
To kick off our fall winery outfit ideas, let’s start with a casual, foolproof look.
Distressed jeans paired with a cozy flannel shirt is a comfortable, classic pairing perfect for wineries.
The distressed jeans add a relaxed, laidback vibe that’s ideal for walking around the vineyards and tasting wines.
Look for a pair in a rich fall hue like hunter green or burgundy.
Dark washes are nice as well.
Go for a slim straight or skinny cut, which is both chic and figure-flattering.
Distressed details like ripped knees, fraying hems, and faded accents enhance the casual effect.
In terms of flannel, choose one in an autumnal buffalo plaid print that complements your jeans.
Look for soft cotton or cotton-blend flannels for maximum comfort.
Oversized styles work well, as do cropped cuts.
Tuck your flannel into your jeans or leave it loose over top.
Finish the look with ankle booties or chunky lace-up boots.
A felt cowboy hat adds a cute finishing touch.
For accessories, layered pendant necklaces look pretty.
Go for delicate gold and silver chains with pendants like initials, stones, or charms.
Cuff bracelets in sculptural metals like bronze or gunmetal add visual interest.
Lastly, don’t forget those sunnies.
Cat-eye shapes and angular frames flatter most face shapes.
When the sunshine fades, you can switch to a beanie or fedora if it gets chilly.
This casual flannel and jeans outfit is my personal go-to winery look.
I’ll wear distressed white jeans with a classic black and red buffalo plaid flannel shirt.
My favorite accessories are pendant necklaces layered together and a simple silver cuff bracelet.
For shoes, I love Chelsea boots or lace-up booties in cognac leather.
The look is comfortable, stylish, and perfect for an afternoon of wine tasting.
Sweater Dress & Tall Boots
For our next idea, embrace the sweater dress trend.
Knit sweater dresses are a chic winery option that combines style and comfort.
Go for a slim fitting midi length style in a rich fall tone like mustard, cranberry, or forest green.
Cashmere, merino wool, or cotton blend fabrics feel luxe while keeping you warm.
Pair your sweater dress with OTK (over-the-knee) boots in suede or leather.
Tan, black, and chestnut shades complement most sweater dress colors.
OTK boots add leg-lengthening height while the closed toe and block heel make them comfortable for winery walking.
Layer a longline duster cardigan over your sweater dress when the temperature dips.
Choose a color that matches your dress or boots.
A neutral like camel, gray, or oatmeal works with any outfit.
For extra warmth, you can even wear leggings underneath your dress.
Finish this look with a crossbody bag in a rich fall shade like burnt orange, olive, or maroon.
Inside, carry a large scarf to use as a wrap if needed.
Simple gold hoops, a delicate necklace, and stacking bracelets or bangle make chic accent pieces.
Don’t forget the cat-eye sunnies to complete your stylish winery outfit.
For this look, I’d wear an off-the-shoulder cranberry sweater dress with tan suede OTK boots and a gray duster cardigan.
My accessories include a black crossbody bag, gold hoops, and a pendant necklace.
The sweater dress and boots combination is flattering and comfortable for an afternoon of wine tasting.
Faux Leather Leggings & Chunky Knit
Leather leggings paired with an oversized sweater is sleek winery look.
Faux leather leggings offer stretch and comfort while providing an edgy vibe.
Black or merlot shades work nicely for fall.
Look for leggings with faux front pockets to enhance the leather pants effect.
On top, choose an oversized chunky knit sweater in cotton, wool, or acrylic blends.
Turtlenecks, cowl necks, and funnel necks are all chic options.
Play with autumnal hues like orange spice, cream, olive, and rust.
Neutrals like gray, ivory, and black also pair well with leather leggings.
Tuck your sweater into your leggings or leave it loosely flowing overtop.
Ground the look with Chelsea boots or lace-up combat style boots.
Black leather or suede finishes complement the leggings perfectly.
For chilly winery days, finish with a long wool coat in camel or black.
For accessories, a leather crossbody bag continues the faux leather look.
Hoop earrings, stacked gold bangles, and a few delicate necklaces make nice complements.
Don’t forget to carry a scarf in your bag too.
Finish with mirrored or blue-light glasses for a futuristic edge.
I’d style this outfit with black faux leather leggings, an oversized rust orange sweater, and black suede boots.
My accessories include a black leather crossbody, small hoops, bangle bracelets, and a lightweight scarf for later.
The leather leggings and chunky sweater balance an edgy yet comfortable look that’s great for wineries.
Printed Wrap Dress & Ankle Boots
Nothing feels more effortlessly chic than a wrap dress.
Flowy, printed wrap dresses work perfectly for wineries.
Look for midi or maxi length dresses in airy fabrics like jersey, rayon, or polyester.
Florals, paisleys, and boho prints evoke a romantic winery vibe.
Deep fall hues like ruby, emerald, ochre, and sapphire feel seasonal.
Pair your printed wrap dress with ankle boots to offset the femininity with a touch of edge.
Pointed toes and chunky block heels are comfortable for walking around the vineyards.
Black and tan leather or suede finishes suit most prints.
Layer up this dressy look with a jean or leather jacket on top.
Cropped motorcycle styles work well.
For colder weather, finish with tights and a long wrap coat.
Carry a large leather tote bag that fits easily over your shoulder and can hold your scarf, camera, etc.
Inside, pack a pashmina scarf to use as a shawl with your dress.
Complete the look with dainty layered necklaces, stackable rings, and medium-sized hoops or drop earrings.
cat-eye sunnies keep your eyes protected in style.
I’d wear this look with a long ruby jersey wrap dress, black leather pointy toe ankle boots, and a light wash denim jacket on top.
My accessories include a cognac leather tote, gold jewelry, and a printed pashmina for later.
The floral wrap dress and edgy ankle boots make a chic pairing for winery style.
Corduroy Pants & Oversized Sweater
Corduroy pants are back in style and perfect for fall winery adventures.
Look for wide-leg and flare leg silhouettes, which feel dressy and vintage-inspired.
Rich fall shades like mustard, cinnamon, hunter green, burgundy, and navy exude cozy charm.
High-waisted fits feel both chic and comfortable.
On top, pair an oversized, slouchy sweater.
Turtlenecks and cowl necks are perfect for keeping cozy.
Opt for soft, luxe fabrics like cashmere, merino wool, or thick cotton blends.
Neutrals like cream, gray, and black complement corduroy beautifully.
For a pop of color, opt for eggplant, scarlet, or bright white instead.
Choose a sweater length that hits just below your pant waistband.
Finish this charming look with short leather boots.
Ankle and calf height styles allow your wide-leg pants to drape nicely.
Block heels or lug soles offer stability on winery grounds.
For accessories, carry a large tote bag that can hold your sweater when the temperature rises.
Inside, pack a lightweight scarf too.
Complete your outfit with delicate layered necklaces with initial or coin pendants.
A stack of mixed metal bangles adds shine.
For earrings, go with sculptural climbers or oversized hoops.
Finally, cat-eye or rounded sunglasses polish off your chic winery ensemble.
I’d style this outfit with mustard wide-leg corduroys, a cream oversized turtleneck sweater, and black short ankle boots.
My accessories include a cognac leather tote, gold pendant necklaces, mixed metal bangles, and blue-light sunglasses.
It’s a comfortable, retro-inspired look ideal for wander wineries.
Cable Knit Tunic & Tall Boots
Cable knit sweaters make a chic statement at wineries.
Look for a tunic length sweater in alpaca, wool, acrylic, or cotton blends.
Neutrals like ivory, charcoal, black, and caramel work year-round.
For pops of color, try ruby, emerald, cobalt, or ochre shades.
Cowl neck, funnel neck, and mock neck silhouettes feel modern and sophisticated.
On bottom, pair with faux or real leather leggings.
Shiny black finishes complement cable knits beautifully.
For added warmth, you can layer fleece-lined tights underneath.
Complete the look with tall boots that hit over or at the knee.
Almond and pointed toe silhouettes feel refined.
Block heels or riding boot soles offer comfort and stability.
Stick with black or brown leather for the most versatility.
Stay warm with a long wool coat.
Camel, black, and red shades make chic top layers.
Accessorize with a leather crossbody bag, circle scarf, and oversized sunnies.
Delicate gold, pearl, or beaded jewelry provides pretty accents.
This outfit is easy to recreate.
I’d wear a cream cable knit cowl neck tunic sweater with black faux leather leggings and black leather tall boots.
My accessories include a red wool coat, black crossbody bag, oversized sunnies, and pearl drop earrings for chic winery style.
Jumpsuit & Ankle Boots
For our next idea, consider a jumpsuit.
Stylish yet comfortable, jumpsuits work perfectly for wineries.
Look for slim fitting styles with long sleeves and wide or straight legs.
Jersey, ponte, and faux wrap fabrics drape beautifully.
Deep fall hues like forest green, burgundy, navy, and mustard look posh.
Pair your jumpsuit with heeled booties, flats, or ankle boots.
Pointed toes elongate your silhouette.
Block heels or lug soles offer stability for walking.
Luxe leather or velvety suede finishes complement most jumpsuits.
Finish with a long tie belt or wide belt at the waist.
This defines your shape beautifully.
Layer a short jacket, long cardi, or trench coat on top for warmth.
Accessorize with a crossbody bag, statement earrings, and sunnies.
Don’t forget your scarf for later!
I’d style a navy jersey jumpsuit with tan tie belt, black suede pointy toe booties, and a red wool moto jacke
My accessories include a black leather crossbody, gold hoops, and cat-eye shades.
It’s a chic yet no-fuss option for looking fab at the winery.
Bell Sleeve Blouse & Skinny Jeans
Few top styles feel as effortlessly chic as the bell sleeve.
Flowy bell sleeve blouses pair perfectly with skinny jeans for winery wanderings.
Look for silky styles in satin, chiffon, or crepe.
Billowy bishop sleeves with elasticized cuffs create dramatic volume.
The best colors for fall include cranberry, mustard, army green, emerald, and sapphire.
On bottom, dark wash skinny jeans balance the blouse’s floaty shape.
A high-waisted fit is both comfortable and figure-flattering.
Look for rich fall washes like burgundy, olive, eggplant, and navy.
Distressed details like fading and knee rips add casual edge.
Ground the look with ankle booties, ballet flats, or low block heels.
Pointed toes complement the skinny jeans.
Soft suede, matte leather, and velvet finishes work well.
Stay warm with a moto jacket, trench coat or longline cardigan on top.
Accessorize with dainty layered necklaces, small hoops or studs, and a leather crossbody.
Finish with a circle scarf and rectangular sunnies.
For this look, I’d pair an emerald green bell sleeve blouse with black high-waisted skinny jeans and tan suede ankle booties.
My accessories include a black moto jacket, gold jewelry, an ivory circle scarf, and blue light sunnies.
It balances dressy and casual perfectly.
Faux Fur Vest & Ankle Pants
Make a stylish statement by rocking a faux fur or shearling vest.
Soft faux fur vests lend instant luxury to any winery outfit.
Look for shaggy styles or colors like ivory, chocolate, and black.
Cropped silhouettes work nicely over dresses, skirts, and pants.
Pair your vest with ankle pants or slim straight jeans.
Rich fall hues like ruby, olive, eggplant, and mustard complement most furs.
High-waisted fits feel polished.
Add a turtleneck, mock neck, or sleeveless blouse underneath.
Tuck your top in or leave it flowing over the waistband.
On your feet, go for heeled booties, riding boots, or low block heel boots.
The ankle height complements cropped pants perfectly.
Luxe suede and matte leather work well.
Top off your look with a floppy wool hat for added coziness.
Accessorize with a crossbody bag, draped scarf, and statement jewelry.
Oversized sunnies or blue light glasses add modern edge.
I’d style this outfit with a cream faux shearling vest, forest green ankle pants, and tan suede booties.
My accessories include a felt floppy hat, burnt orange pashmina scarf, gold hoops, and cat-eye sunnies.
The faux fur vest makes any outfit instantly chic for wineries.
Tulle Skirt & Fuzzy Sweater
For a feminine winery look, try pairing a tulle skirt with a cozy fuzzy sweater.
A-line tulle skirts have a romantic, ballerina-inspired vibe.
Look for lengths that hit just below, at, or above the knee.
Rich fall shades like crimson, emerald, chocolate, and black work beautifully.
On top, layer a fuzzy sweater.
Oversized fuzzy sweaters balance the tulle skirt’s feminine shape.
Choose plush mohair, angora, or wool-blend knits for softness.
Turtlenecks and cowl necks keep you extra cozy.
Opt for cream, gray, blush, or black to let the skirt stand out.
Tuck or half-tuck your sweater in a layered effect.
Finish the outfit with short boots.
Chunky Chelsea boots, riding boots, or lug sole ankle boots complement the look.
Stay warm with a wool moto jacket or longline cardigan on top.
Accessorize with a mini bag, delicate jewelry pieces, and a printed scarf.
Don’t forget your sunnies!
I’d pair a black tulle midi skirt with an oversized cream fuzzy turtleneck sweater and black chunky Chelsea boots.
My accessories include a camel wool moto jacket, black mini bag, layered gold necklaces, leopard print scarf, and blue light sunnies.
It’s a chic yet comfy winery outfit.
Printed Kimono & Straight Leg Jeans
Kimono-style tops lend bohemian flair to any winery outfit.
Flowy printed kimonos in lightweight fabrics like rayon, polyester, and silk are perfect over jeans or leggings.
Look for midi lengths with billowy sleeves, side vents, and tie belt closures.
Floral, paisley, mosaic, and abstract prints all convey a global traveler vibe.
On bottom, pair straight leg or wide leg jeans.
The loose silhouette complements the kimono’s shape.
Dark vintage washes like black, charcoal, and indigo work well.
Look for high-waisted fits that are comfy for hours of wine tasting.
Ground the look with heeled booties, block heel sandals, or low cowboy boots.
Luxe suede and matte leather finishes complement the kimono print.
For accessories, carry a large leather tote bag that can hold your sweater or scarf.
Inside, pack a lightweight pashmina to use as a wrap.
Complete the boho look with woven bracelets, sculptural pendants, and feather earrings.
Don’t forget your sunnies!
I’d wear a navy and white printed kimono with black wide leg jeans and cognac suede block heel sandals.
My accessories include a burnt orange pashmina, tan leather tote, long beaded necklace, and cat-eye sunnies.
It’s an effortless bohemian winery look.
Plaid Skater Skirt & Fisherman Sweater
Let’s add some preppy charm into our winery outfit ideas.
A classic pairing, plaid skirts and fisherman sweaters exude schoolgirl appeal.
Look for skater silhouettes made from lightweight fabrics like ponte, tweed, or felt.
Tartan, buffalo check, and houndstooth prints in rich fall palettes feel seasonal.
Layer a fisherman sweater on top.
Oversized, chunky knit fisherman sweaters balance the skirt’s feminine vibe.
Opt for wool, cotton, acrylic, or nylon blend knits.
Cream, gray, navy, olive, and maroon are perfect fall fisherman shades.
Leave your sweater untucked for a relaxed effect.
Finish with low heeled booties or lace-up boots.
Luxe suede or leather pairs nicely.
Knee high riding boots work well too for added preppy edge.
Pull together the look with a crossbody bag, beanie hat, and printed scarf.
Delicate jewelry like thin layered necklaces and stud earrings polish the outfit off.
Grab your sunnies and you’re ready for a day of winery adventures.
I’d style this outfit with a green and navy plaid skater skirt, cream chunky fisherman sweater left untucked, and black heeled booties.
My accessories include a black crossbody bag, red plaid scarf, beanie hat, and geometric sunnies.
It captures preppy charm and comfort.
Faux Leather Skirt & Striped Sweater
Our last chic fall winery outfit idea features faux leather.
Faux leather skirts lend instant edge to any look.
Go for black, merlot, olive, or chocolate shades.
Mini, midi, and long maxi lengths all work beautifully.
Opt for soft vegan leather with a touch of stretch for comfort.
On top, pair a preppy striped sweater.
Thick horizontal stripe sweaters offer a playful contrast to the skirt.
Choose overseized, slouchy fits in cotton, wool, acrylic blends.
Cream, black, navy, gray, and maroon make classic stripes.
Leave it untucked for a relaxed vibe.
Complete the look with heeled black booties or riding boots.
The closed toe elongates your legs.
Luxe leather finishes complement the faux leather skirt.
Add a moto jacket, wool coat, or trench coat on top for warmth.
Accessorize with a mini bag, chunky scarf, and bold jewelry.
Don’t forget sassy cat-eye sunnies to finish off your chic winery outfit.
I’d wear a black vegan leather midi skirt with an oversized gray and white striped sweater and black heeled booties.
My accessories include a camel trench coat, red mini bag, chunky printed scarf, layered gold necklaces, and angular blue light sunglasses.
It balances edgy and preppy elements for fabulous winery style.
As you can see, wineries offer the perfect opportunity to showcase stylish autumnal outfits.
Use this season as inspiration to assemble chic, comfortable winery looks.
Just add a glass of your favorite wine, and you’re ready for a picturesque day among the vines.
Have fun finding new wineries to explore while showcasing your inner stylist this autumn!
