21 Plus Size Dressy Winter Outfits That Curvy Women Love

Plus size dressy winter outfits that make you look stunning even when temperatures drop below freezing.

Winter doesn’t mean hiding under oversized coats and baggy sweaters. Actually, cold weather gives us amazing opportunities to layer beautifully and create sophisticated silhouettes.

Think luxurious fabrics, rich textures, and strategic layering that celebrates our curves instead of drowning them.

I remember my first office holiday party disaster. Freezing temperatures, a cocktail dress, and zero clue about winter styling. Never again! That night taught me everything about balancing warmth with elegance, comfort with class.

Whether you’re heading to work meetings, date nights, or formal winter events, dressy cold weather fashion is an art form.

It’s about understanding which fabrics work hardest, how to layer without bulk, and finding pieces that transition seamlessly from casual day looks to classy evening ensembles.

The secret? Strategic choices in outerwear, smart layering techniques, and confidence in bold winter colors that pop against snowy backdrops.

These 21 outfits prove that plus size winter fashion can be both practical and absolutely gorgeous.

Must-See: Plus Size Cold Weather Winter Outfits.

21 Plus Size Dressy Winter Outfits

Each look here solves real styling challenges we face during winter months. Don’t forget to check out our styling tips at the end for even more winter fashion wisdom!

1. Plus Size Burgundy Velvet Blazer Professional Winter Outfit

You’ll command respect wearing this sophisticated ensemble featuring a structured burgundy velvet blazer over a cream silk blouse.

Pair with high-waisted charcoal wool trousers that hug your curves perfectly. Add cognac leather ankle boots with a modest heel for professional elegance.

Complete with a delicate gold necklace and matching earrings. This outfit transitions seamlessly from boardroom meetings to after-work networking events.

2. Plus Size Emerald Green Turtleneck Midi Dress Winter Look

Transform your winter wardrobe with this stunning emerald green ribbed turtleneck midi dress that celebrates your silhouette.

The fitted bodice and A-line skirt create an hourglass shape while providing warmth and comfort. Style with black suede knee-high boots and a matching leather belt.

Add gold hoop earrings and a structured black handbag. Perfect for holiday parties or elegant dinner dates during cold weather months.

3. Plus Size Navy Wool Coat Layered Winter Ensemble

Master sophisticated layering with this navy wool double-breasted coat worn over a soft gray cashmere sweater and black ponte pants.

The coat’s tailored silhouette defines your waist while providing essential winter warmth. Complete with black leather loafers featuring gold hardware and a coordinating handbag.

Add a silk scarf in complementary colors for extra elegance. This versatile outfit works beautifully for both casual and professional winter occasions.

4. Plus Size Plum Satin Blouse Office Winter Outfit

Elevate your professional wardrobe with this luxurious plum satin blouse tucked into high-waisted black wool palazzo pants.

The blouse’s subtle sheen adds sophistication while the wide-leg pants create elegant proportions. Style with pointed-toe black pumps and a structured blazer in coordinating charcoal.

Complete with pearl drop earrings and a sleek black tote bag. This outfit combines comfort with boardroom-ready sophistication for winter business meetings.

6. Plus Size Black Ponte Jumpsuit Winter Evening Outfit

Make a statement in this elegant black ponte jumpsuit featuring a fitted bodice and wide legs that create stunning proportions.

The long sleeves provide winter coverage while the fabric’s stretch ensures comfort throughout the evening. Style with metallic heeled sandals and a cropped faux fur jacket for glamour.

Complete with statement earrings and a clutch purse. Perfect for winter cocktail parties, theater nights, or sophisticated social events.

7. Plus Size Forest Green Cardigan Winter Layered Look

Build the perfect winter layered outfit starting with this forest green wool cardigan over a cream turtleneck and dark denim straight-leg jeans.

The cardigan’s longer length creates vertical lines while providing cozy warmth. Add tan suede ankle boots with a block heel and a coordinating crossbody bag.

Include delicate gold jewelry and a patterned scarf. This versatile ensemble works beautifully for weekend activities, casual meetings, or relaxed social gatherings.

8. Plus Size Wine Red Silk Camisole Winter Party Outfit

Transform evening wear for winter with this wine red silk camisole layered under a black velvet blazer, paired with high-waisted black trousers.

The contrast of textures creates visual interest while the colors complement winter’s palette perfectly. Style with black pointed-toe pumps and coordinating jewelry.

Add a structured clutch and a light wrap for transitioning between indoor and outdoor venues. Ideal for holiday parties or sophisticated winter celebrations.

9. Plus Size Charcoal Wool Skirt Professional Winter Look

Create a polished professional appearance with this charcoal wool pencil skirt paired with a soft pink cashmere sweater tucked in neatly.

The skirt’s knee-length cut and fitted silhouette celebrate your curves while maintaining workplace appropriateness. Complete with black leather pumps and a matching blazer for meetings. Add pearl accessories and a structured handbag.

This outfit provides warmth and sophistication for important business presentations or professional networking events during winter.

10. Plus Size Dusty Rose Knit Top Winter Brunch Outfit

Perfect your weekend style with this dusty rose ribbed knit top featuring three-quarter sleeves, paired with high-waisted black leggings and tall brown boots.

The top’s fitted cut highlights your waist while providing comfortable stretch for all-day wear. Layer with a cream wool coat and add gold jewelry for polish. Include a crossbody bag in coordinating leather.

This outfit strikes the perfect balance between comfort and style for winter brunches or shopping excursions.

11. Plus Size Sapphire Blue Wrap Top Winter Dinner Look

Elevate your dinner wardrobe with this sapphire blue jersey wrap top paired with black wide-leg trousers that create elegant proportions.

The wrap style flatters your bust while the rich blue color complements winter’s palette beautifully. Style with black ankle boots featuring metallic details and coordinating jewelry.

Add a structured blazer for transitioning between venues. Perfect for romantic dinners, business meals, or sophisticated gatherings during the colder months.

12. Plus Size Cream Cashmere Sweater Winter Meeting Outfit

Command attention in professional settings wearing this luxurious cream cashmere crew neck sweater with navy straight-leg trousers.

The sweater’s soft texture and neutral color create an approachable yet polished appearance. Pair with cognac leather loafers and a matching belt to define your waist.

Complete with delicate gold jewelry and a structured tote bag. This outfit provides warmth and sophistication for client meetings, presentations, or important business discussions throughout winter.

13. Plus Size Mustard Yellow Cardigan Winter Weekend Look

Brighten winter days with this mustard yellow open-front cardigan worn over a white fitted tee and dark wash straight-leg jeans.

The cardigan’s longer length creates vertical lines while the bold color adds personality to your winter wardrobe. Style with brown ankle boots and a coordinating crossbody bag.

Add layered necklaces and a cozy scarf for extra warmth. Perfect for casual weekend activities, coffee dates, or relaxed social gatherings during colder weather.

14. Plus Size Deep Purple Blouse Winter Networking Outfit

Make networking memorable wearing this deep purple silk blouse tucked into high-waisted charcoal wool trousers.

The blouse’s rich color and luxurious fabric create a professional yet approachable impression. Pair with black leather pumps and a coordinating blazer for meetings. Complete with silver jewelry and a structured handbag.

This outfit combines comfort with confidence, making it ideal for professional networking events, industry conferences, or important business meetings during winter months.

15. Plus Size Taupe Turtleneck Winter Client Meeting Look

Project confidence in client meetings wearing this taupe ribbed turtleneck sweater with black ponte straight-leg pants.

The neutral color palette creates a sophisticated foundation while the turtleneck provides warmth and coverage. Style with black leather ankle boots and a coordinating blazer when needed.

Add gold jewelry and a structured tote bag. This versatile outfit works perfectly for client presentations, business consultations, or professional meetings throughout the winter season.

16. Plus Size Rust Orange Sweater Winter Social Outfit

Stand out at social gatherings in this rust orange crew neck sweater paired with high-waisted dark denim and cognac leather knee-high boots.

The sweater’s rich autumn-inspired color complements winter styling while the fitted cut celebrates your silhouette. Add layered gold jewelry and a matching handbag for polish.

This outfit works beautifully for dinner parties, cultural events, or sophisticated casual gatherings during colder months.

17. Plus Size Ivory Silk Blouse Winter Theater Outfit

Prepare for elegant evenings with this ivory silk blouse featuring subtle pearl buttons, paired with black wide-leg trousers and heeled ankle boots.

The blouse’s lustrous fabric catches light beautifully while maintaining sophisticated appeal. Add a black wool coat for warmth and coordinating jewelry for sparkle.

Complete with a structured clutch and light wrap. Perfect for theater nights, symphony performances, or other cultural events that require polished winter attire.

18. Plus Size Olive Green Tunic Winter Shopping Look

Create the perfect shopping outfit with this olive green tunic sweater worn over black leggings and comfortable ankle boots with moderate heels.

The tunic’s longer length provides coverage and comfort while the rich color adds sophistication to casual wear. Layer with a coordinating cardigan and add gold jewelry for polish.

Include a handbag for hands-free convenience. This outfit combines style with practicality for winter shopping trips or casual weekend activities.

19. Plus Size Coral Pink Cardigan Winter Coffee Date Outfit

Brighten winter coffee dates with this coral pink open-front cardigan layered over a cream fitted tee and dark wash jeans.

The cardigan’s soft color and relaxed fit create an approachable, feminine appearance while providing warmth. Style with brown ankle boots and coordinating accessories.

Add delicate jewelry and a crossbody bag for casual elegance. This outfit strikes the perfect balance between comfort and style for informal meetings, coffee dates, or weekend social activities.

20. Plus Size Steel Gray Sweater Winter Gallery Opening Look

Make an impression at cultural events wearing this steel gray cashmere sweater with black straight-leg trousers and pointed-toe flats.

The sweater’s sophisticated color and luxurious texture create an artistically appropriate appearance. Add interesting jewelry pieces and a structured handbag for gallery browsing.

This outfit provides comfort for standing while maintaining the polish required for gallery openings, museum events, or cultural gatherings during winter.

21. Plus Size Cranberry Red Blouse Winter Holiday Outfit

Celebrate the season in this cranberry red silk blouse paired with high-waisted black trousers and heeled ankle boots.

The blouse’s festive color and elegant drape create perfect holiday styling while maintaining sophisticated appeal. Layer with a black blazer for formal venues and add gold jewelry for sparkle.

Complete with a coordinating clutch for evening events. This outfit works beautifully for holiday parties, seasonal celebrations, or festive gatherings throughout the winter months.

22. Plus Size Chocolate Brown Sweater Winter Book Club Look

Create intellectual elegance with this chocolate brown crew neck sweater worn with cream-colored straight-leg trousers and cognac leather loafers.

The earthy color palette creates a scholarly, approachable appearance while the fitted sweater celebrates your silhouette. Add layered necklaces and a structured tote bag for carrying books.

Include a coordinating cardigan for extra warmth. Perfect for book clubs, lecture series, or educational events that require thoughtful, comfortable winter styling.

23. Plus Size Peacock Blue Cardigan Winter Volunteer Outfit

Serve your community in style wearing this peacock blue open-front cardigan over a white fitted tee with dark wash jeans and comfortable ankle boots.

The cardigan’s vibrant color adds personality while the practical styling allows for active participation. Layer with coordinating accessories and add a handbag for convenience.

Include comfortable yet stylish footwear for extended wear. This outfit combines approachable style with practical comfort for volunteer work, community events, or charitable activities.

24. Plus Size Golden Yellow Blouse Winter Celebration Outfit

End winter celebrations beautifully in this golden yellow silk blouse tucked into high-waisted navy trousers, paired with nude heeled pumps.

The blouse’s warm color creates a celebratory mood while the classic styling maintains elegance. Add coordinating jewelry and a structured handbag for polish.

This outfit works perfectly for milestone celebrations, achievement ceremonies, or special occasions that require sophisticated styling during the winter season.

10 Step Styling Tips for Plus Size Dressy Winter Outfits

Step 1: Master the Foundation Layer Game

Let me tell you something about winter layering – it starts with what nobody sees. Your foundation layer makes or breaks everything else. I learned this the hard way during a Chicago winter wedding.

Silk or moisture-wicking base layers are absolute lifesavers. They keep you warm without adding bulk, and honestly? They make you feel luxurious from the inside out.

Choose seamless options in neutral tones that won’t show through your dressy pieces. Trust me, when you’re comfortable underneath, you radiate confidence on top.

This foundation creates the smooth silhouette you want for dressy occasions.

Step 2: Invest in Structure-Savvy Outerwear

Here’s where most of us go wrong – we buy coats that swallow us whole. Been there, done that, looked like a walking sleeping bag! Your winter coat should enhance your silhouette, not hide it completely.

Look for tailored wool coats with defined waistlines or belted options that create an hourglass shape. A-line coats work beautifully too.

The key is finding outerwear that gives you structure while providing warmth. Remember, you can always layer underneath, but you can’t fix a shapeless coat.

Quality matters here because a well-structured coat transforms your entire winter wardrobe.

Step 3: Embrace Strategic Color Psychology

Winter doesn’t mean living in black and gray forever! Actually, this season gives us permission to play with rich, luxurious colors that complement snowy backdrops.

Deep jewel tones like emerald, sapphire, and burgundy look absolutely stunning against winter’s palette. These colors also photograph beautifully for holiday parties and work events.

I remember wearing a deep plum dress to a winter gala – the compliments didn’t stop coming!

Dark colors are naturally slimming, but don’t be afraid of metallics or even winter white. The contrast creates visual interest and makes you stand out in the best way possible.

Step 4: Perfect Your Texture Mixing Skills

This is where winter styling gets really fun – mixing textures creates depth and visual interest that’s impossible to achieve in summer.

Think about pairing smooth silk with chunky knits, or adding velvet touches to wool pieces. The contrast between different fabrics adds sophistication to any dressy outfit.

I love combining matte and shiny textures too. A cashmere sweater with leather pants? Pure elegance. Velvet blazer over silk blouse? Instant glamour.

The key is choosing textures that complement each other rather than compete. This technique makes even simple outfits look expensive and thoughtfully put together.

Step 5: Navigate the Art of Proportion Play

Understanding proportions changed my entire approach to winter dressing. When you’re layering for warmth, balance becomes crucial. If you’re wearing a voluminous top, pair it with fitted bottoms.

Oversized sweater? Try it with skinny jeans or leggings. The goal is creating visual balance that flatters your curves instead of overwhelming them.

I used to think bigger meant better for hiding, but actually, strategic fitting celebrates our shapes beautifully. Don’t forget about vertical lines – they’re your best friend for creating length and elegance in winter outfits.

Step 6: Discover Your Signature Accessory Strategy

Accessories are winter’s secret weapons, and I mean that literally! The right accessories can transform a basic outfit into something special.

Scarves aren’t just for warmth – they’re styling tools that add color, texture, and visual interest around your face.

Statement jewelry works harder in winter because it contrasts beautifully against dark fabrics. Boots become major style statements too.

I have this one pair of knee-high boots that makes me feel like I can conquer anything. The trick is choosing accessories that serve dual purposes – looking fabulous while keeping you comfortable in cold weather.

Step 7: Master Indoor-to-Outdoor Transition Dressing

This might be the most practical tip I can share!

Winter events often involve multiple temperature changes, and your outfit needs to work everywhere. I learned this during a holiday party where I was freezing outside but overheating inside.

Layer strategically so you can remove pieces without ruining your look. Cardigans, blazers, and wraps are perfect for this. Choose pieces that look intentional whether you’re wearing them or carrying them.

Your outfit should look complete at every stage of undressing. This approach keeps you comfortable and confident no matter where the evening takes you.

Step 8: Shop Smart – Finding the Best Plus Size Winter Brands

Let’s talk about where to actually find these amazing pieces! Target’s Ava & Viv line has seriously stepped up their winter game.

Torrid remains my go-to for trendy pieces that understand curves. For investment pieces, I love Eloquii and Universal Standard – their quality is worth every penny.

Lane Bryant has fantastic work-appropriate options. Online, ASOS Curve offers international styles that feel fresh and modern.

Don’t sleep on Nordstrom Rack either – you can find designer pieces at better prices.

The key is building relationships with brands that consistently fit your body well. Once you find your favorites, stick with them but stay open to trying new options.

Step 9: Perfect Your Evening-to-Work Versatility

The best winter pieces pull double duty, and honestly, who has money for completely separate wardrobes? I focus on pieces that transition easily from professional to party.

A good blazer transforms a simple dress from day to night. Swap your work flats for heels, add statement earrings, and you’re ready for drinks after work.

Midi dresses work particularly well for this strategy. During the day, add a cardigan and practical shoes.

For evening, remove the cardigan, add heels and bold lipstick. This approach maximizes your wardrobe investment while keeping you stylish for every occasion.

Step 10: Build Your Confidence Through Fit Mastery

Here’s the truth nobody talks about – the best styling tip is wearing clothes that actually fit your body right now. Not the size you want to be, not the size you used to be, but your current beautiful self.

I wasted years wearing ill-fitting clothes thinking it would hide my size. Wrong approach entirely! When clothes fit properly, everything looks more expensive and intentional.

Don’t be afraid to tailor pieces – a simple hem or waist adjustment can transform an okay outfit into something spectacular.

Your confidence shows when you’re comfortable in your clothes, and that confidence is the most attractive accessory you can wear.

Final Thoughts

Listen, mastering plus size dressy winter outfits changed everything for me, and it will for you too.

I remember standing in my closet last december, crying because nothing felt right. Now? I actually look forward to getting dressed when it’s freezing outside.

These outfits are your roadmap to feeling unstoppable during the coldest months. You’ve got this, beautiful. Winter won’t know what hit it when you step out looking absolutely incredible.