21 Plus Size Winter Skirt Outfits That Curvy Women Love

Craving plus size winter skirt outfits that actually flatter your curves while keeping you cozy? You’ve found your fashion salvation.

Let me tell you something – I used to think winter meant hiding my beautiful curves under baggy sweaters and boring pants. What a mistake that was!

Winter skirts became my secret weapon for staying stylish when temperatures drop.

Picture this: you’re walking into that holiday party feeling absolutely radiant in a sleek satin midi skirt paired with tights and boots.

Or imagine conquering Monday morning in a trendy pleated skirt that moves with confidence. These aren’t just daydreams, honey – they’re totally achievable winter looks.

Winter fashion for us curvy women doesn’t mean sacrificing style for warmth.

Whether you’re drawn to casual jean skirts with cozy sweaters, classy maxi styles that flow beautifully, or chic short skirts with statement tights, cold weather becomes your runway.

Long winter skirts create elegant silhouettes, while trendy patterns add personality to gray winter days.

I’ve discovered that the right winter skirt transforms everything. It’s about finding pieces that celebrate your body while keeping you comfortable during chilly months.

From office-appropriate looks to weekend casual vibes, these outfit combinations prove that fashion rules are meant to be broken.

Must-See: Plus Size Winter Work Outfits.

21 Plus Size Winter Skirt Outfits

Don’t forget to check out our styling tips section at the end for extra inspiration and practical advice!

1. Plus Size Winter Leopard Print Pleated Skirt Outfit

Pair a knee-length leopard print pleated skirt with a black turtleneck sweater and chocolate brown knee-high boots. Add a camel-colored wool coat for warmth.

This bold combination balances animal print with neutral tones, creating sophistication while keeping you cozy during cold weather adventures.

2. Plus Size Winter Burgundy Velvet Midi Skirt Outfit

Style a rich burgundy velvet midi skirt with a cream cable-knit sweater and gold ankle boots. Layer a long black cardigan for extra warmth.

The luxurious velvet texture adds elegance to winter gatherings, while the neutral sweater keeps the look grounded and wearable for various occasions.

3. Plus Size Winter Plaid Wool A-Line Skirt Outfit

Choose a gray and red plaid wool A-line skirt with a black fitted sweater and burgundy riding boots. Complete with a matching red scarf and black wool peacoat.

This classic combination channels prep school chic while providing warmth and structure that flatters your silhouette beautifully.

4. Plus Size Winter Emerald Green Satin Pencil Skirt Outfit

Rock an emerald green satin pencil skirt with a black silk blouse and pointed-toe ankle boots. Add a tailored black blazer and statement pearl earrings.

This sophisticated ensemble works perfectly for holiday parties or dinner dates, combining festive color with timeless elegance and winter-appropriate layering.

5. Plus Size Winter Tweed Circle Skirt Outfit

Wear a charcoal tweed circle skirt with a dusty pink cashmere sweater and brown leather knee boots. Layer a long cream trench coat for polish.

The structured tweed provides warmth while the circle silhouette creates beautiful movement, making this perfect for professional settings or weekend brunches.

6. Plus Size Winter Corduroy Mini Skirt Outfit

Style a camel corduroy mini skirt with opaque black tights, a forest green sweater, and suede ankle boots. Add a long denim jacket (optional) for casual vibes.

The corduroy texture provides warmth and visual interest, while the mini length with tights creates a youthful, trendy look that’s surprisingly winter-friendly.

7. Plus Size Winter Navy Pinstripe Maxi Skirt Outfit

Combine a navy pinstripe maxi skirt with a white button-down shirt and cognac leather boots. Layer a camel wool cardigan for warmth.

This professional look elongates your silhouette while the pinstripes add subtle pattern. Perfect for office settings where you want to look polished yet comfortable all day.

8. Plus Size Winter Faux Leather Wrap Skirt Outfit

Pair a black faux leather wrap skirt with a chunky gray sweater and combat boots. Add a long burgundy cardigan for contrast.

The edgy leather texture combined with cozy knits creates an unexpected but stylish contrast that works beautifully for casual weekends or evening events with friends.

9. Plus Size Winter Houndstooth Straight Skirt Outfit

Choose a black and white houndstooth straight skirt with a red turtleneck and black ankle boots. Complete with a black wool coat and red handbag.

This timeless pattern adds sophistication to your winter wardrobe while the straight silhouette creates clean lines that flatter your figure perfectly.

10. Plus Size Winter Metallic Pleated Midi Skirt Outfit

Style a rose gold metallic pleated midi skirt with a black cashmere sweater and nude heeled boots. Layer a long black coat for elegance.

The metallic finish catches light beautifully during dark winter days, while the pleated texture adds movement and the midi length provides warmth and coverage.

11. Plus Size Winter Paisley Print Maxi Skirt Outfit

Wear a burgundy paisley print maxi skirt with a cream turtleneck sweater and tan suede boots. Add a long brown cardigan for layering.

The intricate paisley pattern brings visual interest to winter’s neutral palette, while the maxi length provides maximum warmth and creates an elongating effect.

12. Plus Size Winter Quilted Midi Skirt Outfit

Combine a navy quilted midi skirt with a white sweater and brown riding boots. Layer a tan trench coat for sophistication.

The quilted texture provides insulation while adding unique visual appeal. This practical yet stylish combination works perfectly for running errands or casual lunch dates during colder months.

13. Plus Size Winter Tartan Plaid A-Line Skirt Outfit

Rock a red and green tartan plaid A-line skirt with a black turtleneck and black knee boots. Complete with a red wool coat and plaid scarf.

This festive combination embraces winter holidays while the A-line silhouette flatters your curves and the tartan pattern adds traditional Scottish charm.

14. Plus Size Winter Sequined Pencil Skirt Outfit

Pair a black sequined pencil skirt with a silver sweater and metallic ankle boots. Add a black faux fur stole for glamour.

The sequins catch winter light beautifully while providing festive sparkle. Perfect for New Year’s parties or special winter celebrations where you want to shine and feel absolutely stunning.

15. Plus Size Winter Chenille Knit Skirt Outfit

Style a dusty blue chenille knit skirt with a cream cable sweater and cognac ankle boots. Layer a long gray cardigan for warmth.

The soft chenille texture feels luxurious against your skin while providing cozy comfort. This combination creates a relaxed yet put-together look perfect for weekend activities or casual meetings.

16. Plus Size Winter Brocade Midi Skirt Outfit

Choose a gold brocade midi skirt with a black silk blouse and pointed heels. Add a black velvet blazer for sophistication.

The ornate brocade pattern adds richness to winter events while the midi length provides elegant coverage. This ensemble works beautifully for theater nights or upscale dinner parties.

17. Plus Size Winter Denim Maxi Skirt Outfit

Wear a dark wash denim maxi skirt with a burgundy sweater and brown ankle boots. Complete with a long camel coat and cognac accessories.

The denim provides durability and casual appeal while the maxi length offers warmth. This versatile combination transitions easily from day activities to evening gatherings.

18. Plus Size Winter Jacquard A-Line Skirt Outfit

Combine a forest green jacquard A-line skirt with a cream turtleneck and tan knee boots. Layer a brown wool coat for polish.

The intricate jacquard weave adds texture and visual interest while the rich green color complements winter’s earthy palette beautifully, creating sophisticated seasonal style.

19. Plus Size Winter Faux Suede Pencil Skirt Outfit

Pair a chocolate brown faux suede pencil skirt with a ivory sweater and matching brown boots. Add a long tan cardigan for layering.

The suede texture feels luxurious while providing warmth. This monochromatic brown palette creates a rich, cohesive look that’s perfect for professional settings or weekend brunches.

20. Plus Size Winter Herringbone Straight Skirt Outfit

Style a gray herringbone straight skirt with a navy sweater and black ankle boots. Complete with a long navy coat and matching scarf.

The classic herringbone pattern adds sophisticated texture while the straight silhouette creates clean lines. This timeless combination works beautifully for business meetings or lunch dates.

21. Plus Size Winter Embellished Midi Skirt Outfit

Rock a black midi skirt with gold embellishments, paired with a gold sweater and black heeled boots. Add a black faux fur jacket for glamour.

The embellishments catch light beautifully during winter’s shorter days while adding festive sparkle. Perfect for holiday parties where you want to make a memorable impression.

22. Plus Size Winter Cable Knit Maxi Skirt Outfit

Choose a cream cable knit maxi skirt with a burgundy turtleneck and brown riding boots. Layer a long brown cardigan for extra warmth.

The cable knit texture provides cozy comfort while the maxi length offers maximum coverage. This comfortable yet stylish combination perfect for casual winter outings or cozy gatherings.

23. Plus Size Winter Polka Dot Midi Skirt Outfit

Wear a navy polka dot midi skirt with a white sweater and red ankle boots. Complete with a red wool coat and navy accessories.

The playful polka dots add whimsy to winter dressing while the classic color combination creates timeless appeal. This cheerful ensemble brightens up dreary winter days beautifully.

24. Plus Size Winter Textured Twill Skirt Outfit

Combine a olive green textured twill skirt with a cream sweater and tan combat boots. Add a long brown jacket for layering.

The twill weave provides durability and subtle texture while the olive color offers a fresh alternative to winter’s typical dark palette, creating an unexpectedly chic seasonal look.

10 Helpful Styling Tips For Plus Size Winter Skirt Outfits

1. Master the Foundation Layer Philosophy

I learned this the hard way during a freezing Chicago winter – your foundation determines everything.

Start with high-quality shapewear or a well-fitted slip that smooths your silhouette without creating uncomfortable bulges.

Think of it as your canvas. The right foundation prevents that dreaded static cling and creates clean lines under your skirt.

I always choose seamless options in nude tones that match my skin. This invisible layer becomes your secret weapon for confidence.

When your foundation feels secure, you walk differently – with purpose and poise. Don’t skimp here, ladies. A good foundation piece costs more upfront but transforms every single outfit.

2. Perfect Your Proportional Balance Game

Here’s something fashion magazines never tell you – balance isn’t about hiding curves. It’s about celebrating them strategically.

If you’re wearing a voluminous A-line skirt, pair it with a fitted top to create that coveted hourglass silhouette. Conversely, if your skirt hugs your hips beautifully, try a slightly looser sweater that still shows your waistline.

I’ve found that tucking in sweaters or using a belt helps define that crucial waist point. The goal isn’t to minimize – it’s to create visual harmony. Your eye should travel smoothly up and down your silhouette without getting stuck anywhere.

Remember, proportion is personal. What works on Instagram might not work for your unique body shape.

3. Layer Like a Cozy Style Scientist

Layering in winter requires strategy, not just throwing on more clothes. Start with thin, breathable base layers that won’t add bulk. Then add your main pieces thoughtfully.

I love pairing a fitted turtleneck under an oversized cardigan with my favorite midi skirt. The key is varying textures and weights.

A chunky knit cardigan over a silk blouse creates interesting visual depth. Don’t forget about proportions when layering – if your top layer is long, make sure your skirt peeks out beautifully underneath.

I always do the “sit test” before leaving home. Can I sit comfortably without my layers bunching awkwardly? Layering should enhance your silhouette, never overwhelm it.

4. Choose Winter-Appropriate Fabrics Wisely

Not all fabrics are created equal for winter skirt wearing. I’ve shivered through too many events in the wrong materials.

Wool blends, heavy cotton, corduroy, and ponte knits become your best friends. These fabrics provide warmth while maintaining structure.

Avoid thin materials that cling uncomfortably or show every line underneath. Jersey knits can work, but choose heavier weights that drape beautifully.

I’m obsessed with ponte – it feels like wearing pajamas but looks completely polished. Velvet and brocade add luxury for special occasions.

Always check care instructions before buying. Nothing ruins a winter wardrobe like discovering your favorite skirt needs dry cleaning after every wear. Practical doesn’t mean boring – it means smart.

5. Master the Art of Strategic Color Selection

Winter doesn’t mean surrendering to all-black everything, though black is undeniably chic.

I’ve discovered that rich jewel tones – emerald, sapphire, burgundy – photograph beautifully and complement most skin tones. Earth tones like camel, chocolate, and olive green feel sophisticated yet approachable.

Here’s my secret: start with one statement color piece, then build around it with neutrals. A emerald green skirt becomes the star when paired with cream and gold accessories.

Don’t ignore patterns completely – subtle plaids, tasteful florals, and classic stripes add visual interest without overwhelming your silhouette.

Color psychology matters too. Wearing colors that make you feel confident shows in your posture and smile.

6. Navigate Hosiery and Undergarment Essentials

Let’s talk about the unsexy stuff that makes everything else look amazing. Quality tights and stockings are non-negotiable for winter skirt wearing.

I always buy extras because runs happen at the worst possible moments. Control-top tights smooth your silhouette while providing warmth. For thinner skirts, shapewear shorts prevent chafing and create smooth lines.

Invest in seamless underwear that won’t create visible lines. I learned this lesson photographing outfits – every bump and line shows up. Consider thigh-high stockings with shorter skirts for a vintage-inspired look.

The right undergarments should feel invisible while making you look incredible. Don’t let uncomfortable foundations ruin your confidence throughout the day.

7. Select Perfect Footwear for Function and Style

Footwear makes or breaks winter skirt outfits. I’ve fallen on icy sidewalks wearing the wrong shoes – not cute.

Ankle boots work with almost every skirt length and style. Knee-high boots create stunning silhouettes with midi and mini skirts.

For professional settings, low-heeled pumps with good tread provide polish without sacrificing stability. Weather matters more than fashion sometimes.

Keep stylish snow boots handy for truly nasty days. Boot height affects leg proportions significantly. Ankle boots elongate legs, while over-the-knee styles create dramatic looks. Consider your lifestyle realistically.

Those gorgeous heeled boots might look amazing, but if you’re walking six blocks in snow, choose function over pure aesthetics. Comfort builds confidence naturally.

8. Shop Smart at Plus Size Friendly Brands

Finding quality plus-size winter skirts requires knowing where to look. Torrid consistently offers trendy options in extended sizes.

Lane Bryant provides classic professional pieces that last for years. ASOS Curve ships internationally and stocks unique designs. Eloquii specializes in contemporary plus-size fashion with excellent fit.

Universal Standard focuses on size inclusivity and quality construction. Don’t overlook mainstream retailers like Target’s Ava & Viv line or Old Navy’s plus section for affordable basics.

Online shopping requires understanding return policies – always check before ordering. I maintain a spreadsheet of my measurements from different brands because sizing varies dramatically.

Facebook groups and Instagram accounts dedicated to plus-size fashion provide honest reviews and styling inspiration from real women.

9. Accessorize to Enhance Your Winter Silhouette

Accessories transform basic outfits into stunning ensembles. Wide belts define your waist beautifully over sweaters and cardigans.

Statement necklaces draw attention upward and add sparkle to solid-colored tops. Scarves provide warmth while introducing pattern and color.

I collect scarves because they’re affordable ways to update existing outfits. Handbag proportions matter – tiny purses can look overwhelmed, while oversized bags might throw off your balance.

Choose bags that complement your scale naturally. Don’t forget about hair accessories during winter – headbands and clips keep hair neat under hats and scarves.

Jewelry should be visible but not competing with your outfit. Less is often more effective than piling on multiple statement pieces simultaneously.

10. Develop Your Personal Winter Skirt Styling Formula

After years of trial and error, I’ve developed my personal formula that works consistently.

I always start with one statement piece – usually the skirt – then build around it with neutrals and textures. This prevents overwhelming combinations while ensuring interesting outfits.

I keep a running list of successful combinations on my phone for busy mornings. Photographing outfits helps identify what works and what doesn’t.

Your formula might be completely different from mine, and that’s perfect. Maybe you prefer monochromatic looks or bold pattern mixing.

The key is identifying your preferences and creating a system that makes getting dressed easier and more enjoyable.

Confidence comes from understanding what makes you feel amazing, then repeating those successful elements consistently.

Final Thoughts

These plus size winter skirt outfits aren’t just clothing combinations – they’re your armor against a world that doesn’t always celebrate our curves.

I’ve watched too many beautiful women hide behind oversized sweaters, convinced winter means sacrificing style.

But here’s what I know: when you step out wearing that perfect skirt outfit, something magical happens. You walk taller. You smile brighter.

You remember that your body deserves beautiful clothes in every season. Your confidence becomes contagious, inspiring other women to embrace their own winter style journey.