10 Winery Outfit Ideas Perfect for a Chilly Winter Day You’ll Actually Love Wearing

Chilly-weather wine tasting is a vibe—twinkle lights, barrel rooms, and cozy pours. The trick? Dressing warm enough to linger outdoors without losing any style points indoors. These outfits strike that sweet spot: polished, practical, and camera-ready for every sip-and-scenery moment.

Expect delicious textures (hello, wool and cashmere), smart layering, and footwear that handles gravel paths without sacrificing chic. Grab a glass, and let’s build your perfect winter winery wardrobe—one outfit at a time.

1. Cashmere Sweater + Midi Skirt Magic With Weather-Ready Boots

This look wins every time: soft cashmere on top, swishy midi on the bottom, and boots that love a vineyard stroll. It’s elevated without being precious, and the midi length keeps you warm while still feeling feminine. Great for tastings, tours, and that golden-hour view.

Outfit Pieces:

• Cream cashmere turtleneck (slightly relaxed fit)
• Satin or wool-blend midi skirt in burgundy, forest green, or bronze
• Weatherproof heeled ankle boots in black or caramel
• Wool wrap coat in camel or charcoal
• Thermal tights (black or skin-tone)
• Gold hoop earrings and a delicate pendant necklace
• Structured leather crossbody

Styling Tips:

• Tuck the sweater lightly at the front to define your waist and balance the skirt’s volume.
• Choose a midi that hits mid-calf to pair perfectly with ankle boots—no strange gap.
• Opt for matte tights with a slight compression for warmth and a sleek look.
• Keep jewelry warm-toned to complement winery lighting and rich winter colors.

Going somewhere with a breeze? Add a blanket scarf in a tonal plaid. For daytime, swap the pendant for layered chains; for dinner, slip on a bold cuff bracelet. This outfit takes you from tasting room to dinner reservation effortlessly.

2. Tailored Wool Blazer + Straight Jeans That Look Effortlessly Polished

When you want classic-meets-cool, a structured blazer and straight-leg denim deliver. It’s comfortable for walking the vines but sharp enough for a barrel tasting selfie. Add a knit underneath and you’re cozy without the bulk.

Outfit Pieces:

• Double-breasted wool blazer in herringbone or tweed
• Fine-knit merino crewneck in charcoal or cream
• High-rise straight-leg jeans (dark wash, minimal distressing)
• Leather Chelsea boots with lug soles
• Longline wool scarf in a muted stripe
• Leather belt and stud earrings
• Medium structured tote

Styling Tips:

• Choose a blazer that skims the hips for flattering warmth and clean lines.
• Stick to a dark wash jean—more polished, more forgiving, and more winter-friendly.
• Lug-soled Chelseas handle gravel and damp ground. Win-win.
• Pop the collar of your knit slightly for effortless texture under the blazer lapel.

Heading from tasting to town? Swap the scarf for a silk neckerchief for a French-ish twist. For extra warmth, layer a thin thermal tee under your knit. This is the outfit you’ll wear on repeat, trust me.

3. Chic Puffer + Knit Dress That Feels Like A Warm Hug

If you want the comfort of a blanket without looking like one, this is it. A sleek knit dress under a modern puffer is warm, flattering, and totally winery-appropriate. It’s also ridiculously easy to dress up with boots and accessories.

Outfit Pieces:

• Matte, mid-length puffer coat in olive, black, or deep navy
• Ribbed knit midi dress with a mock neck
• Knee-high leather boots with a block heel
• Thermal slip or heattech layer under the dress
• Thin leather belt to define the waist
• Wool beanie and cashmere gloves
• Small crossbody or belt bag

Styling Tips:

• Belt the dress over the puffer for a street-style moment, or keep it internal for a cleaner line.
• Pick a dress with substantial ribbing—it smooths and insulates better.
• Match boots to dress or coat for a long, lean look.

Great for wineries with outdoor fire pits or patio tastings. Want a softer vibe? Choose a dress in heathered taupe or forest and add gold hoops. It’s as comfortable as it gets without sacrificing style.

4. Monochrome Moment In Winter Whites (Yes, You Can)

Winter whites at a winery? Absolutely. A tonal cream-and-beige palette looks luxe, photographs beautifully, and makes your glass of cab look like an accessory. Plus, monochrome feels instantly put-together with zero effort.

Outfit Pieces:

• Cream turtleneck sweater (chunky or fisherman knit)
• Beige tailored wool trousers or cream wide-leg jeans
• Tan suede ankle boots (water-resistant spray recommended)
• Camel wrap coat or cream topcoat
• Textured scarf in oatmeal or sand
• Gold layered necklaces and pearl studs
• Structured mini satchel

Styling Tips:

• Mix textures—ribbed knits, soft wool, suede—to keep monochrome from feeling flat.
• Hem trousers to skim boot tops so hems don’t drag on damp ground.
• Use subtle makeup and rosy cheeks to complement the soft palette.

Perfect for special tastings or a winery lunch. If you’re worried about spills, pick a marled cream knit or a flecked tweed trouser. The tonal effect stays elevated and surprisingly practical.

5. Cabin-Core Layers: Flannel, Vest, And Lug-Sole Boots

Rustic-chic without going full lumberjack. This layered look is warm, playful, and made for crisp air and vineyard paths. It’s also easy to adjust as you head from outdoors to barrel rooms.

Outfit Pieces:

• Brushed flannel shirt in deep green, burgundy, or navy plaid
• Lightweight merino base layer (long-sleeve)
• Quilted or down vest in black or olive
• Straight or slim black jeans
• Lug-sole hiking-style boots (leather or suede, waterproofed)
• Beanie and wool socks
• Crossbody phone bag

Styling Tips:

• Size the flannel slightly oversized for movement; tuck just the front for shape.
• Keep colors tonal (greens with olives, burgundy with browns) for a cohesive look.
• Leave the vest open to avoid bulk, or zip halfway for a defined waistline.

Ideal for casual tasting rooms and vineyard tours. Want a touch of polish? Swap hiking boots for leather Chelseas and add a sleek watch. Cozy, functional, and totally photogenic.

6. The Elevated Jumpsuit + Long Coat Combo

One-and-done dressing that looks like you tried. A tailored jumpsuit under a dramatic coat is sleek, warm, and easy to accessorize. It’s perfect when you want to look pulled together without fussing with separates.

Outfit Pieces:

• Long-sleeve tailored jumpsuit in black, charcoal, or deep merlot
• Wool maxi coat in camel or black
• Heeled sock boots or pointed-toe ankle boots
• Thermal camisole underneath
• Statement earrings and a sleek bracelet
• Compact crossbody or envelope clutch

Styling Tips:

• Define the waist with a belt—leather for structure, satin for glam.
• Choose a cropped or tapered leg to showcase your boots.
• Keep the palette minimal to let the silhouette shine.

Great for a winery dinner, private tasting, or special event. If it’s extra cold, add sheer thermal tights under the jumpsuit and a cashmere scarf. Effortless elegance, seriously.

7. Cozy Sweater Dress + Shearling Accents For Soft, Snug Style

Meet your coziest tasting-day outfit. A sweater dress with shearling details is warm, sweet, and still chic. It’s the outfit that makes you want to linger by the fireplace with a glass of pinot.

Outfit Pieces:

• Chunky sweater dress (knee or midi length) in heather oatmeal or charcoal
• Shearling-lined ankle boots or platform clogs with socks
• Wool blend coat or shearling-trim jacket
• Fleece-lined tights
• Oversized scarf in a soft check
• Minimal rings and stud earrings
• Medium leather shoulder bag

Styling Tips:

• Balance a chunky dress with sleek boots, or go full cozy with shearling—just keep accessories simple.
• Choose a dress with side slits for movement and a bit of shape.
• Use a thin belt to define the waist if the knit is very oversized.

Perfect for casual wineries and outdoor patios. Want variety? Swap the coat for a long cardigan under a topcoat. The texture play looks luxe and feels like a hug.

8. Parisian-Inspired: Striped Knit, Trench, And Wine-Ready Red Lip

Classic, chic, and so easy to throw on. A striped knit with a trench and dark denim feels timeless—but winterized with smart layers and boots. It’s the outfit that says, “I taste notes of blackberry and style.”

Outfit Pieces:

• Striped merino or cashmere sweater (black/cream or navy/cream)
• Thermal long-sleeve base layer
• Dark straight or slim jeans
• Water-resistant trench coat or wool trench
• Block-heel ankle boots or sleek loafers with socks
• Beret or structured beanie
• Red lipstick and gold hoops
• Crossbody satchel

Styling Tips:

• Layer a thin puffer vest under the trench if it’s extra chilly—no one will see it.
• Keep the jeans cropped to show just a hint of sock above your boots.
• Choose a soft-matte red lip to avoid smudging on glass rims.

Great for urban wineries or tasting rooms with a design edge. For a slightly dressier take, add a silk scarf tied at the neck. It’s simple, striking, and travel-friendly.

9. Statement Coat + All-Black Base For Instant Drama

Let your coat do the talking. A bold color or textured coat over an all-black base makes winter dressing feel exciting. It photographs beautifully and keeps you warm without overthinking the rest.

Outfit Pieces:

• Statement wool coat (bold color, check, or faux-fur texture)
• Black turtleneck (cashmere or merino)
• Black coated jeans or black ponte trousers
• Black heeled boots (weatherproof)
• Black leather belt
• Chunky gold earrings and a sleek watch
• Compact black crossbody

Styling Tips:

• Keep the base fitted so the coat can shine without bulk.
• Match metals—gold with warm coats, silver with cool tones—for harmony.
• Coated jeans add subtle shine that elevates the monochrome base.

Ideal for holiday winery trips and festive events. Want softer drama? Choose a dusty rose or deep teal coat. The all-black base keeps it sophisticated and warm.

10. Quilted Skirt Set + Knee Boots For Feminine Warmth

Skirt sets aren’t just for spring. A quilted or padded skirt with a matching jacket or sweater is cozy, structured, and unexpectedly chic for winter wine tasting. It’s feminine but practical—your legs stay warm, your boots do the walking.

Outfit Pieces:

• Quilted A-line midi skirt in olive, black, or merlot
• Matching quilted jacket or soft cashmere sweater
• Knee-high boots with a block heel
• Thermal tights
• Wool wrap coat layered over
• Leather gloves and drop earrings
• Small structured handbag

Styling Tips:

• Balance quilted volume with a fitted top or a defined waistline.
• Choose boots that match the skirt tone for a lengthened silhouette.
• Keep accessories minimal so the texture remains the star.

Perfect for scenic vineyards and tasting flights. Swap the jacket for a sweater in cream or charcoal for contrast, or add a slim belt over the coat to cinch everything together. Warm, pretty, and polished.

How To Stay Warm Without Bulking Up

• Start with breathable base layers (merino or heattech) under sweaters and dresses.
• Choose wool or cashmere blends for real warmth without weight.
• Prioritize weatherproof boots with traction—gravel and grass can be slick.
• Carry a scarf you can wrap around your shoulders inside chilly barrel rooms.

Accessories That Make The Outfit (And Handle The Weather)

• Structured crossbodies and small totes keep hands free for tastings.
• Gloves and beanies in neutrals go with everything; add a pop of color through lipstick or scarves.
• Jewelry should be simple but intentional—gold hoops, a watch, a cuff.

Color Pairings That Love Vineyard Backdrops

• Forest green with camel and cream for a woodsy, luxe vibe.
• Burgundy with charcoal and gold for a rich, festive look.
• Navy with sand and black for timeless polish.
• Winter whites with tan boots and camel coats for quiet luxury.

Ready to sip in style? Mix and match these ideas to fit your vibe, your weather, and your itinerary. With smart layers, luxe textures, and the right boots, your winter winery day will look as good as it tastes—cheers to that.