Tired of hiding your curves under bulky winter layers at wine tastings? Let’s transform your plus size winter winery outfits from basic to breathtaking!
Are you feeling stuck about what to wear for a winter wine tasting? I get it.
As a plus size fashion expert who’s spent years helping women embrace their curves, I know the struggle of finding that perfect blend of style and comfort for winery visits.
Let me tell you about my first winter winery tour. I showed up in an unflattering oversized sweater, thinking it would keep me warm. Boy, was I wrong!
Not only was I uncomfortable, but I missed out on great photos because I felt self-conscious.
That day taught me something important – we curvy girls deserve to feel confident and look fabulous while sipping our favorite wines.
Winter winery outfits are tricky for everyone, but they bring unique challenges for plus size women.
We need pieces that keep us cozy without adding unnecessary bulk, outfits that transition well from indoor tastings to outdoor vineyard tours, and styles that make us feel like the queens we are.
Make sure to stick around for the styling tips at the end…
I’m sharing some game-changing secrets about layering, accessorizing, and choosing the right fabrics for winter winery visits.
Trust me – these tips will change how you approach dressing for wine tastings forever.
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21 Plus Size Winter Winery Outfits
That’s why I’m excited to share these 21 carefully curated plus size winter winery outfits with you.
The best part? These outfits aren’t just about looking good – they’re about feeling comfortable and confident while you’re creating memories.
Whether you’re planning a romantic wine tasting date or a fun afternoon with your girlfriends, you’ll find options that make you feel amazing.
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1. Vintage Black Lace Midi Dress with White Collar
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The black lace hugs your curves in all the right places – um, can we talk about how that midi length is perfect?
You get the white collar and cuffs for that classic look, plus… those heels!
The whole outfit gives me Wednesday Addams meets corporate boss vibes. Not gonna lie, this is what I’d wear to make an entrance at that winery holiday party.
2. Disco Queen Sparkly Black PJ Set + Gold Chain Bag
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The sparkly dots catch light with every move – kinda like your own personal disco ball, right? That loose-fit shirt and those flow pants? Pure magic for fulling your glam.
I love how the gold accessories – wait, peep that chain bag! – add pop. You’ll steal the show without feeling squeezed in.
No more choosing between style and breathing room. This is what I’d rock when I want to feel fancy but also want to eat and drink at the winery. You feel me?
3. Navy Flow High-Low Dress + Mustard Bag + Silver Cuffs
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This navy dress works overtime! The loose fit gives you room to move – no more pulling or tugging.
I love how the high-low hem moves with each step, and those statement cuffs? Pure drama! The mustard bag pops against the navy, and clear sandals keep things breezy.
You’ll walk into the fields of winery feeling like a queen. Who says comfort can’t look fancy?
4. Boss Babe Pinstripe Peplum Blazer + Wide Pants + Pink Flats
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The pinstripe blazer cinches at the waist – and oh, that belt creates an hourglass shape, and those black pants flow like water with each step.
The peplum cut hides any tummy concerns while the long blazer lengthens your frame.
Real talk – this is what I’d wear to make my entrance at a classy CEO’s wine party… don’t you think?
5. Evening Look Sheer Mesh Top with Wide-Leg Pants
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The sheer black mesh top features crisp white collar and cuffs, creating a play on a tuxedo shirt. The mesh reveals a black bustier underneath, adding mystery.
Those wide-leg black pants give you room to move and dance. A small white handbag pulls the look together, while red shoes add a pop of color.
Perfect for sipping wine with friends or a fancy night out. You’ll feel confident knowing this look hits all the right style notes.
6. Vintage-Inspired Tea Dress in Burgundy Taffeta
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You’ll make an entrance in this 1950s-style dress that hits every winter wine tasting note.
The tea-length skirt swishes when you walk, and a wrapped shawl neckline drapes your shoulders with grace.
The matching bag and dotted heels pull the monochrome look together. This outfit channels pure Hollywood glamour for your next wine country visit.
7. Burgundy Velvet Midi Dress with Cream Cable-Knit Cardigan
Picture yourself in a rich burgundy velvet midi dress with a sweetheart neckline and puff sleeves. Layer it with a cream cable-knit cardigan that hits at mid-thigh.
Add cognac leather knee-high boots with a block heel for comfort. A chunky gold statement necklace draws the eye up, while thermal tights keep you warm.
Top it off with a camel beret and matching leather gloves.
8. Dark Wash Bootcut Jeans with Metallic Western Blazer
Start with high-waisted dark wash bootcut jeans that hug your curves.
Tuck in a black turtleneck bodysuit and layer with a champagne-colored metallic western blazer with concho buttons. Slip on pointed-toe cowboy boots in distressed brown leather.
A turquoise statement belt adds pop, while a shearling-trimmed denim jacket provides warmth. Complete with a wide-brim black felt hat.
9. Emerald Chunky Knit Sweater Dress with Black Faux Vest
Embrace a sweater dress in emerald green chunky knit with a mock neck and balloon sleeves.
Layer with a black faux vest that hits at the waist. Black over-the-knee boots elongate your legs, while a silver pendant necklace adds sparkle.
A matching emerald beret and fingerless gloves in soft angora complete this mountain-chic look.
10. Victorian Lace Blouse with Plum Corset Vest & Black Maxi Skirt
Rock a high-necked Victorian-style blouse in ivory lace under a plum-colored corset vest.
Pair with a flowing black maxi skirt featuring subtle metallic threads. Add lace-up ankle boots in burgundy leather. Layer with a dramatic cape coat in charcoal wool.
Pearl drop earrings and a vintage-inspired brooch add timeless charm.
11. Leopard Midi Skirt with Black Turtleneck & Rust Leather Moto
Mix a leopard print midi skirt in warm browns with a black ribbed turtleneck sweater.
Add a rust-colored leather moto jacket for edge. Black pointed-toe ankle boots with gold hardware keep it sleek. Layer delicate gold necklaces and add tortoiseshell sunglasses.
A structured black leather tote completes the look.
12. Plum Velvet Suit with Gold Camisole & Patent Leather Accents
Work a plum velvet blazer with black satin lapels over matching wide-leg pants.
Layer a metallic gold silk camisole underneath. Add black patent leather block heels and a matching clutch with gold hardware.
Statement earrings in geometric shapes catch the light. Top with a cream wool coat for outdoor transitions.
13. Midnight Blue Velvet Kimono with Metallic Bodysuit & Palazzo Pants
Layer a midnight blue wrap kimono with burnout velvet patterns over wide-leg black palazzo pants.
A fitted mock-neck bodysuit in silver metallic fabric adds shine. Black platform Chelsea boots give height without sacrificing comfort.
Add multiple silver bangles and a long pendant necklace. Top with a structured black wool fedora.
14. Bronze Sequin Wide-Leg Jumpsuit with Chocolate Leather Trench
Your curves shine in this bronze sequin jumpsuit featuring palazzo legs and deep V-neck, perfectly balanced with a chocolate leather trench.
The structured jumpsuit includes built-in shapewear panels that smooth while showing off your shape.
Platform ankle boots in cognac suede add height without sacrificing comfort. Gold chain belt cinches the waist while pearl drops frame your face.
15. Boho Paisley Palazzo Set with Faux Fur Collar Coat
This matching palazzo set showcases a rich jewel-toned paisley print in teals and purples, cut to float over curves.
The blazer features subtle waist definition and extended lapels. A black silk camisole provides coverage, while the champagne faux fur collar coat adds drama.
Metallic pointed mules elongate your legs, and the emerald box bag adds punch.
16. Modern Pinstripe Cigarette Pants with Metallic Blazer
Navy pinstripe pants with silver threading hug your curves before tapering at the ankle.
The rose gold metallic blazer creates structure with strong shoulders and a nipped waist. A black silk bow blouse softens the look while patent leather loafers with chunky gold chains ground it.
Crystal necklaces and cat-eye sunglasses finish this power look.
17. Rock Leather Pencil Skirt with Metallic Mesh Top
The burgundy leather pencil skirt hugs your curves with strategic panels and a back slit for movement.
A gold metallic mesh top layered over a black camisole adds edge while providing coverage. The cropped velvet blazer features crystal buttons that catch light.
Studded black boots and layered chains complete this rock-inspired ensemble.
18. Asian Brocade Pants with Asymmetric Blouse
Golden brocade wide-leg pants featuring traditional dragon motifs elongate your silhouette.
The black asymmetric blouse creates drama with one statement sleeve while skimming your curves. A deep red velvet cropped jacket adds structure.
Platform sandals lengthen legs while jade statement earrings and a metallic minaudière bring cultural elements together.
19. French Tweed Cape with Leather Leggings
A dramatic black and gold tweed cape creates mystery while leather leggings show off your curves.
The cream silk high-neck blouse features delicate ruffles that peek through the cape’s opening.
Metallic gold ankle boots add glamour while a black beret brings Parisian charm. The quilted leather crossbody adds practicality.
20. Studio 54 Velvet Tuxedo with Crystal Mesh Tank
Sapphire blue velvet tuxedo with satin lapels creates a striking silhouette.
The jacket’s tailored cut emphasizes your waist while flared pants elongate legs. A crystal mesh tank adds sparkle beneath.
Silver platform sandals and tennis bracelets catch disco lights. The white faux fur stole drapes dramatically for grand entrances.
21. Moroccan Embroidered Maxi Coat with Satin Pants
A black wool maxi coat showcases vibrant floral embroidery while deep purple satin pants flow underneath.
The fitted black turtleneck creates a sleek base. Bronze metallic boots peek out while walking. Layered ornate gold necklaces and oversized gem earrings add exotic flair.
Every movement creates elegant drama.
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➜ Useful Styling Tips for Plus Size Winter Winery Outfits
Here are my tried-and-true styling tips for creating the perfect plus size winter winery outfit:
1. Start with a Solid Foundation: Listen, your base layer can make or break your whole look. I learned this the hard way at my first wine tasting.
Choose a fitted cami or long-sleeve bodysuit that smooths without squeezing. This gives you a clean canvas to build on and prevents bunching when you layer.
Plus, if you get warm inside the tasting room, you’ll still look put together when you remove layers.
2. Master the Art of Layering: Think of layering like wine pairing, it’s all about balance.
Start with your base, add a cozy sweater or cardigan, and top with a statement coat.
I love wearing a wrap sweater because it creates shape and lets me adjust throughout the day.
The key is choosing pieces that work together but also look good separately.
3. Choose Wine-Friendly Fabrics: Here’s something I wish someone had told me sooner – dark colors aren’t the only option for wine tastings.
But pick fabrics that can handle an accidental splash. Wool blends, ponte knit, and dark patterns hide potential wine marks better than light silks or linens.
Trust me, this tip will let you focus on enjoying the wine instead of worrying about stains.
4. Pick Strategic Footwear: You’ll thank me for this one. Wineries mean lots of walking – through cellars, vineyards, and between tasting rooms.
I opt for block heels or fancy boots with grip. They give height without the wobble, especially after a few tastings!
Make sure they’re broken in and comfortable for standing.
5. Add Practical Accessories: Let’s talk accessories that work for wine tasting.
A crossbody bag keeps your hands free for holding wine glasses and taking notes. Add a scarf that doubles as a wrap for outdoor tours.
I also bring a small clutch for my tasting notes and phone – it fits perfectly in my bigger bag.
6. Consider the Venue: Each winery has its own vibe. Check their dress code before you go. Some are casual, others lean formal.
I usually aim for smart casual – think dark jeans paired with a nice sweater and boots.
It works everywhere and lets you focus on the experience rather than feeling overdressed or underdressed.
7. Plan for Temperature Changes: This is crucial – you’ll move between warm tasting rooms and cool cellars all day.
I create looks with pieces I can remove or add easily. A sleeveless dress with a cardigan and coat works great. You can adjust your layers without losing style points.
Remember, comfort leads to confidence, and that’s what makes any outfit shine.
Final Thoughts
You know what I’ve learned after years of helping women find their perfect plus size winter winery outfits? Style isn’t about rules – it’s about feeling like yourself.
I remember watching a client transform when she put on an outfit that made her feel beautiful.
Her shoulders straightened, her smile widened, and she owned that tasting room! That’s what I want for you.
Your curves tell your story, and your winter winery outfit should help you tell it.
Whether you’re swirling a glass of cabernet or strolling through vineyards, wear what makes you feel unstoppable.
Because when you feel confident, you shine brighter than any wine bottle in that cellar. So go ahead – dress up, show up, and sip that wine like the queen you are!
I’m Theresa! A devoted lover of women’s fashion. My mission is to curate the latest trends and timeless fashion for women. I want to inspire confidence and creativity through fashion, helping women express their unique personalities with every outfit.