10 Chic Vineyard Winter Outfits You’ll Want to Copy Immediately for Cozy-cute Sips

You’re here for warm wine, rolling views, and the kind of winter outfits that make people whisper, “Where’d she get that?” Good. Vineyard season doesn’t end with summer—winter tastings are a vibe: fewer crowds, richer reds, and the coziest layers. These 10 looks are built for chilly breezes between barrels, toasty patios, and that golden hour stroll through the vines.

We’re talking polished, practical, and photogenic—without freezing or looking overdone. Ready to plan your tasting flight the stylish way? Let’s pour the fits.

1. Heritage Wool Coat + Cashmere Dress That Serves Old-World Romance

This outfit is all about quiet luxury with movement. A swishy cashmere sweater dress under a structured heritage wool coat reads elegant but approachable—perfect for sipping by the fireplace or touring the barrel room. It’s timeless, ridiculously comfortable, and looks even better with a glass in hand.

Outfit Pieces:

• Double-breasted wool coat in camel or deep charcoal
• Cashmere or merino sweater dress in cream, heather gray, or forest green
• Knee-high leather boots with a block heel
• Opaque thermal tights (black or chocolate)
• Structured leather crossbody or mini satchel
• Gold hoop earrings and a delicate pendant
• Soft knit scarf in a complementary neutral

Styling Tips:

• Choose a coat with subtle shoulder structure and a tailored waist—think slightly oversized but still streamlined.
• Keep the dress length midi; it’s warmer and looks luxe with tall boots.
• Match boot and tight colors to elongate your legs and keep the silhouette clean.
• Go for “soft glam” makeup: rosy cheeks, a berry lip, and brushed-up brows.

Wear this for winter wine pairings, anniversary tastings, or anytime you want “effortless elegance.” Swap the scarf for a silk neckerchief in burgundy for a subtle winery nod. If it’s extra cold, layer a thin thermal top under the dress and no one will know—except your toasty self.

2. Puffer Chic + Monochrome Knit Set For Warmth Without Bulk

Think outdoorsy, but make it sleek. A streamlined puffer over a matching knit set gives you that put-together monochrome look without sacrificing warmth. It’s sporty-meets-chic and ideal for walking the property or outdoor tastings.

Outfit Pieces:

• Glossy or matte mid-length puffer jacket in black, olive, or espresso
• Ribbed knit sweater + matching knit skirt (midi length)
• Weatherproof leather ankle boots with lug soles
• Wool beanie in a matching or tonal color
• Tech-friendly leather gloves
• Minimalist backpack or belt bag worn crossbody
• Chunky chain bracelet for a hint of shine

Styling Tips:

• Keep everything tonal for that lengthening effect—think charcoal on charcoal or olive on olive.
• Half-tuck the sweater into the skirt to define your waist under the puffer.
• Pick a puffer with a cinchable waist or subtle quilting to avoid the marshmallow look.
• Elevate with sleek boots instead of sneakers—still comfy, more vineyard-ready.

Perfect for windier days or when the tasting room spills outdoors. If you want an alternative to the skirt, swap for knit pants in the same set—still chic, extra cozy. A pair of wool socks peeking above the boots feels intentional and functional.

3. Tweed Blazer + Dark Denim That Says “I Know My Pinot”

This is classic with a twist: a tweed blazer paired with inky denim and a polished knit. It’s tailored without trying too hard—great for private tours, meet-the-winemaker events, or that casual-chic sweet spot most vineyards lean into.

Outfit Pieces:

• Tweed or herringbone blazer in brown mix or charcoal
• Fine-gauge turtleneck or crewneck in cream or soft taupe
• Dark-wash straight-leg jeans with minimal whiskering
• Leather Chelsea boots or almond-toe ankle boots
• Leather belt with a refined buckle
• Small shoulder bag or structured crossbody
• Pearl studs or simple gold hoops

Styling Tips:

• Cuff the jeans just enough to show the boot shaft—one clean roll looks intentional.
• Go for a slightly boxy blazer fit with strong lapels; it photographs beautifully.
• Layer a silk camisole under the knit if you run cold; a heat-tech base layer is your secret weapon.
• Keep accessories minimal—tweed already provides texture and interest.

Wear this for tastings that lean educational or for a cozy lunch in the vineyard bistro. For extra warmth, drape a wool scarf in a soft check over the blazer. If you want a pop, add a berry lip or a leather bag in dark wine—on theme, obviously.

4. Après-Ski-Inspired Fair Isle + Leather Leggings For Cozy Edge

Channel the slopes without leaving the vines. A Fair Isle sweater brings winter charm, while leather leggings add polish and a little attitude. It’s playful, warm, and surprisingly flattering—especially balanced with chunky boots.

Outfit Pieces:

• Fair Isle or patterned wool sweater in natural tones with a hint of color
• Faux-leather leggings or coated skinny jeans
• Lace-up hiker boots with treaded soles
• Shearling-trimmed jacket or cropped puffer
• Ribbed beanie and matching mittens
• Crossbody phone bag for hands-free sipping
• Simple stud earrings to keep attention on the knit

Styling Tips:

• Choose a sweater that hits at mid-hip; oversized but not sloppy keeps proportions balanced.
• Leggings look best with a thicker, matte finish for day—avoid ultra-shiny for tastings.
• Pick a boot with some heft to ground the look; cream or tan laces add winter charm.
• Keep hair down or in a loose low pony with the beanie—effortless and chic.

Great for outdoor tasting flights, mulled wine pop-ups, or winery markets. Want to dress it up? Swap hiker boots for sleek heeled ankle boots and add a long wool coat. A red knit lip balm ties it all together—festive but still casual.

5. Sleek Jumpsuit + Longline Coat For Minimalist Power

If you want a one-and-done outfit that looks instantly expensive, this is it. A tailored jumpsuit under a longline coat reads sophisticated and modern, and it’s an absolute dream for photos. Plus, no tucking or adjusting—just clean lines and easy comfort.

Outfit Pieces:

• Tailored jumpsuit in black, espresso, or deep green (long sleeves or layered with a knit)
• Longline wool coat in camel, sand, or black
• Pointed-toe ankle boots or block-heel boots
• Leather belt to define the waist (optional)
• Statement earrings—think sculptural gold
• Compact top-handle bag or sleek crossbody
• Cashmere scarf for extra warmth

Styling Tips:

• Look for a jumpsuit with a defined waist and slight flare at the leg for balance.
• Layer a thin turtleneck underneath if yours is short-sleeved; tonal colors keep it chic.
• Keep the palette simple—two to three colors max for that minimalist vibe.
• Go monochrome for ultimate impact: all black with a camel coat is foolproof.

Perfect for date-night tastings, wine club events, or any setting that calls for understated glam. If you need traction for a vineyard walk, switch to lug-sole boots. Add a berry velvet lip and you’re done—seriously, it’s that good.

6. Quilted Barn Jacket + Midi Skirt For English-Countryside Meets Napa

This look nails that rustic-chic sweet spot. The quilted barn jacket has countryside charm, while a swishy midi skirt keeps it feminine and elevated. It’s relaxed but refined, ideal for all-day tasting itineraries with a bit of walking.

Outfit Pieces:

• Quilted barn jacket in olive, tan, or navy
• Midi skirt in satin, wool, or pleated fabric
• Fitted ribbed turtleneck or long-sleeve tee
• Stack-heel ankle boots or sleek riding boots
• Wool beret or structured felt hat (wind permitting)
• Crossbody saddle bag
• Layered gold necklaces

Styling Tips:

• Tuck your knit into the skirt and belt lightly at the waist, then add the jacket for shape.
• Choose a midi length that hits mid-calf; it’s practical for walking and looks elegant.
• Opt for boots in chocolate or cognac to play nicely with earthy tones.
• If it’s breezy, satin or pleated skirts photograph beautifully with movement—just avoid ultra-thin fabric.

Wear this for winter picnic tastings, scenic strolls, or tours that pass through the vines. For colder days, swap the skirt for wool culottes or a knit midi and add thermal tights. A patterned scarf in checks or floral adds countryside charm without feeling costume-y.

7. Tonal Knit Layers + Shearling Vest For Cozy Texture Play

Texture is the star here. Tonal knits in varying weights paired with a shearling or faux-shearling vest create instant depth and a plush, touchable look. It’s warm, tactile, and very “I woke up in a vineyard cottage.”

Outfit Pieces:

• Shearling or faux-shearling vest in cream or tan
• Chunky knit sweater in oatmeal, sand, or soft gray
• Wool-blend tailored trousers or knit flares
• Suede ankle boots or clogs with socks
• Knit headband or ear warmers
• Textured tote (bouclé or suede)
• Minimal gold rings

Styling Tips:

• Keep the palette tonal—cream, beige, tan, and sand. It’s chic and low-effort.
• Front-tuck the sweater to show a bit of waist and break up the knits.
• Choose trousers with a slight crop to showcase the boot; add cozy socks in a matching tone.
• A vest with a slightly longer hem elongates the torso and looks more intentional.

Ideal for slow afternoons and pairing flights when comfort is key. For rain-prone vineyards, switch suede to leather and add a waterproof spray. A soft blush and glossy lip bring warmth to all those soft neutrals.

8. Belted Cape + Slim Pants That Turn Heads Between The Barrels

Drama, but make it wearable. A belted cape or poncho draped over slim pants creates that editorial shape without trying too hard. It looks elegant floating through the tasting room and keeps heat trapped where you want it.

Outfit Pieces:

• Wool cape or poncho with a waist belt
• Slim tailored pants or ponte leggings
• Knee-high boots or sleek sock boots
• Leather gloves for a polished finish
• Structured top-handle bag
• Statement ring or cuff bracelet
• Silk scarf tucked at the neck

Styling Tips:

• Balance volume: cape on top, slim on bottom. It’s the formula that never fails.
• Belt at your natural waist or slightly higher to create a flattering line.
• Stick to two colors for impact—think cream and black, or charcoal and camel.
• Wear hair in a low bun or sleek pony to keep the neckline clean and chic.

This is the outfit for special events, long lunches, or when you’re celebrating a big moment. If you’re petite, choose a shorter cape to avoid overwhelming your frame. Add a red wine-toned lipstick to lean into the theme—because why not?

9. Utility Jacket + Sweater Dress + Over-The-Knee Boots For Effortless Cool

When you want a little edge with your elegance, this combo hits. A structured utility jacket tones down a soft sweater dress, while over-the-knee boots add length and warmth. It’s balanced, practical, and low-key sexy in the most vineyard-appropriate way.

Outfit Pieces:

• Cotton-twill or waxed utility jacket with pockets
• Chunky sweater dress in cream, mocha, or olive
• Over-the-knee suede or leather boots with a flat or low heel
• Thermal tights if needed
• Leather crossbody with antique gold hardware
• Wool scarf in checks or stripes
• Small hoop earrings

Styling Tips:

• Pick a dress that hits mid-thigh to about two inches above the boot top—no awkward gaps.
• Keep the jacket slightly cropped or cinched to define your waist.
• If you’re between sizes, size up in the jacket to layer a knit comfortably.
• Monochrome dress and boots will make your legs look a mile long.

Great for vineyard hopping or casual tastings with a side of charcuterie. Want to go more polished? Swap the utility jacket for a trench with a quilted liner. A soft gloss and windproof hairstyle are your windy hillside friends.

10. Velvet Suit + Turtleneck For Festive Firelight Glam

Velvet and wine were made for each other. A velvet suit with a sleek turtleneck whispers holiday elegance and photographs like a dream. It’s luxe, cozy, and just the right amount of extra for winter winery events.

Outfit Pieces:

• Velvet blazer in merlot, midnight blue, or deep evergreen
• Velvet trousers with a straight or slightly flared leg
• Fine-knit turtleneck in black, cream, or charcoal
• Pointed-toe heeled boots or sleek loafers
• Clutch or mini shoulder bag with chain strap
• Bold earrings or a single statement necklace
• Faux-fur stole or wool wrap for extra warmth

Styling Tips:

• Keep the suit tailored—no slouchy fits here. A defined shoulder and clean waist are key.
• Wear the turtleneck fitted to streamline under the blazer; thin merino works best.
• Balance shine: velvet is the star, so keep jewelry minimal but impactful.
• Hem trousers to just graze the top of your shoe for a polished line.

Perfect for candlelit tastings, winter soirées, or any event with live music and long pours. If you want a softer vibe, switch the turtleneck for silk and add a long wool coat. A deep berry lip and brushed waves seal the deal.

How To Navigate Weather And Terrain Without Sacrificing Style

Vineyards can be muddy, windy, and colder than you expect. Always check the forecast and plan for layers. Opt for block heels, lug soles, or sturdy flats over delicate stilettos. Bring a wrap or scarf you can tuck into your bag—tasting rooms can swing warm to cool fast.

Accessory And Beauty Notes That Elevate Everything

• Jewelry: Gold warms up winter palettes; pearls add classic charm.
• Bags: Hands-free crossbodies are ideal. Keep them compact so you’re not juggling.
• Makeup: Think dewy base, flushed cheeks, and a berry or brick lip. Set with a light powder—tasting rooms get toasty.
• Hair: Low buns, loose waves, or half-up styles handle wind gracefully.

Color Pairings That Always Work At A Vineyard

• Wine Tones: Merlot, plum, and rose pair beautifully with cream and camel.
• Earthy Neutrals: Olive, tan, and charcoal feel grounded and photogenic.
• Winter Brights: Forest green, midnight blue, and burnt orange add pop without shouting.

You’ve got options for every kind of winter tasting—from casual firepit flights to festive evening pours. Mix, match, and make them your own. The vines are calling, the pours are generous, and your winter outfit game is about to be unbeatable. Cheers to cozy layers, rich reds, and photos you’ll actually want to post.