
Winter visits to a winery are all about cozy vibes, good wine, and, of course, looking your best while staying warm. Whether you’re enjoying a casual tasting or celebrating a special occasion, having the right outfit can make all the difference.
At Chic Season Style, we’ve put together 11 plus-size winter winery outfits that will help you feel confident and comfortable, without compromising on style. Here are some cozy and chic looks to wear during your next winery visit.

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1. Cozy Knit Sweater & Skinny Jeans

A soft, oversized knit sweater is perfect for keeping warm while looking chic. Pair it with a simple pair of skinny jeans and ankle boots for a casual but stylish look that will keep you cozy all day long. Add a scarf for a little extra warmth and flair.
2. Turtleneck & A-Line Skirt

A fitted turtleneck is a great layering piece for winter. Pair it with an A-line skirt for a feminine look that’s easy to move in. Add tights and knee-high boots to stay warm, and you’ll be ready to sip wine in style.
3. Plaid Flannel Shirt & Denim

For a laid-back look, try a plaid flannel shirt with your favorite pair of denim jeans. This look is perfect for a casual outing and is super comfortable. Finish the outfit with some boots or sneakers to keep things comfy while you enjoy the wine.
4. Faux Fur Vest & Long-Sleeve Top

A faux fur vest is a fun way to stay warm and stylish. Layer it over a fitted long-sleeve top and pair it with black pants or leggings for a sleek, chic look. Add ankle boots and a cozy scarf to complete your outfit.
5. Cardigan & Midi Dress

A cardigan over a midi dress offers both warmth and comfort. Whether your dress is floral, solid, or patterned, a cardigan adds an extra layer of warmth and a stylish touch. Pair with tights and boots to keep your legs warm as you sip and relax.
6. Chunky Knit Sweater & Leather Leggings

Leather leggings bring a touch of edginess to any outfit. Pair them with a chunky knit sweater for a cozy yet bold look. This combination is perfect for when you want to be stylish and comfortable at the same time.
7. Wool Coat & Scarf

A classic wool coat is both warm and timeless. Layer it over a cozy sweater and jeans for a sophisticated yet casual winery look. A wool-blend scarf adds extra warmth, and it’s easy to toss over your shoulders when you’re not sipping wine.
8. Sweater Dress & Tights

A sweater dress is a go-to winter piece that’s easy to dress up or down. Pair it with tights for extra warmth and boots to keep your feet cozy. Whether you’re at a winery or a cozy gathering, this outfit will keep you comfortable and stylish.
9. Quilted Jacket & Wide-Legged Pants

For a more relaxed look, a quilted jacket over a fitted top is perfect. Pair it with wide-legged pants to keep it casual but chic. This outfit is perfect if you want to be comfortable but still look put-together for a day out at the winery.
10. Fitted Blazer & Jeans

A fitted blazer over a simple sweater or shirt can instantly elevate your look. Pair it with jeans for a polished, chic vibe that’s still comfortable. Heeled boots will complete the outfit for a wine-tasting experience you’ll feel confident in.
11. V-Neck Sweater & High-Waisted Skirt

For something more feminine, try a V-neck sweater with a high-waisted skirt. It’s a flattering and easy-to-wear outfit that’s perfect for winter winery visits. Pair it with tights and boots to stay warm and stylish.

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Final Thoughts
Heading to a winery in the winter doesn’t mean sacrificing style for warmth. With these 11 plus-size outfits, you can enjoy a glass of wine while staying cozy and chic. Whether you prefer classic looks like a cozy sweater and jeans or something a bit more polished like a wool coat and skirt, there’s a winter winery outfit that will make you feel fabulous.
At Chic Season Style, we believe in making every woman feel confident, no matter where she’s going. So, next time you’re planning a winery trip, dress in something that makes you feel amazing and enjoy the experience in style. Cheers!