24 Plus Size Winter Legging Outfits (Stay Warm & Stylish)

Ready to rock the coziest plus size winter legging outfits that blend comfort and style effortlessly? Yes, you can rock those curves!

Have you ever stood in front of your mirror, leggings in hand, wondering how to style them for winter without freezing or feeling self-conscious? Trust me, I’ve been there too.

As a plus size fashion enthusiast and stylist who lives in leggings (let’s be real here), I know the struggle of putting together winter outfits that are both warm and stylish.

Winter brings its own set of challenges for us curvy girls, from finding the right layers to creating proportions that make us feel confident.

I remember the day I cracked the code on plus size winter legging outfits.

I was rushing to meet friends for brunch, threw on some leggings with a long sweater, boots, and a scarf.

The compliments I got that day changed my whole perspective on winter fashion. Now, I’m here to share everything I’ve learned about rocking leggings in cold weather.

Here’s the thing – leggings aren’t just loungewear anymore. They’re a versatile foundation for countless winter looks.

Whether you’re heading to work, meeting friends, or running errands, there’s a way to style leggings that’ll make you feel amazing.

The secret? It’s all about the right combinations and knowing a few key styling tricks.

Must-Have: Cold Weather Winter Outfits.

24 Plus Size Winter Legging Outfits

In this guide, I’ll walk you through 24 different ways to wear leggings this winter. These legging outfits are specifically created for our curvy bodies.

We’ll talk about what actually works (and what doesn’t), how to layer without adding bulk, and which pieces you might already have in your closet.

Let’s dive into these game-changing plus size winter legging outfits that’ll keep you warm, comfortable, and looking absolutely gorgeous.

1. Cozy and Casual with an Oversized Hoodie

Grab a soft oversized hoodie and pair it with your favorite black leggings. Toss on a pair of chunky sneakers for running errands or just hanging out.

You’ll feel comfortable and still put-together. Add a crossbody bag to keep things hands-free. Don’t forget a beanie—it’s like a warm hug for your head.

Wondering about layering? Throw on a long puffer coat if it’s chilly. This outfit is all about ease without feeling sloppy.

2. Dressy Vibes with Faux Leather Leggings

Slip into faux leather leggings to instantly elevate your winter look. Pair them with a long tunic-style sweater—bonus points if it covers your hips.

Slide into ankle boots with a low block heel. Need more polish? Add a gold chain necklace or hoop earrings. Heading out? Toss on a tailored wool coat.

This combo works for casual dinner plans or even a movie date. You’ll look sharp but still relaxed.

3. Classic Black-on-Black for Workdays

Pair black leggings with a longline black blazer for a sleek office look. Layer a plain white tee or a light turtleneck underneath.

Step into loafers or pointed flats to keep it work-appropriate. Got meetings? A structured tote bag completes the look.

You might think black-on-black sounds boring, but the textures make it pop. Add a scarf for some warmth, it’ll pull the whole outfit together effortlessly.

4. Sporty and Functional with a Puffer Vest

Layer your leggings with a thermal top and zip up a puffer vest. Lace up some trail shoes or boots if you’re heading outdoors.

Toss your hair into a messy bun for that no-fuss vibe. Feeling cold? Add fingerless gloves so you can still scroll your phone.

This outfit is perfect for winter walks or even grabbing coffee. You’ll stay warm and comfy without overheating indoors.

5. Chic and Simple with an Oversized Button-Up

Throw on an oversized flannel or chambray button-up shirt over your leggings. Roll the sleeves a bit for that lived-in look.

Choose slip-on mules or low-top sneakers for shoes. Tuck the front of your shirt in slightly to define your shape.

Thinking of accessories? A canvas tote works perfectly here. This outfit feels like your go-to when you don’t want to think too hard but still want to look presentable.

6. Layered Look with a Long Cardigan

Drape a long cardigan over your basic leggings and a fitted tank top. Add a matching sneaker to balance the proportions.

Toss on a belt if you want to cinch your waist a little. This outfit gives cozy cabin vibes, perfect for sipping hot cocoa by a fireplace or shopping downtown.

Add a chunky knit scarf for extra warmth. It’s versatile, so you can dress it up or down as needed.

7. Statement Sweater with Bold Prints

Pair your plain leggings with a bold, patterned sweater, it could be argyle, stripes, or even animal print.

Keep the shoes neutral, like white sneakers or gray ankle boots. Add small hoop earrings for a little shine. Need warmth? A solid-colored coat balances the outfit.

This look is playful and grabs attention without trying too hard. Wear it when you’re in the mood to stand out without feeling overdone.

8. Weekend Errands with a Denim Jacket

Start with black or gray leggings and a basic hoodie. Layer on a slightly oversized denim jacket for some structure.

Keep the shoes easy, think slip-on sneakers or boots. Bring a backpack for a practical yet stylish touch. This outfit is great for grocery runs or casual hangouts.

Want more flair? Add a graphic beanie. It’s a no-brainer combo that always feels dependable, like your favorite playlist.

9. Luxe Layers with a Knit Poncho

Slip on a cozy knit poncho over your leggings and a plain top. Knee-high boots make the outfit look polished.

Add a leather satchel for some texture contrast. This is your go-to look for brunch or a casual work meeting.

Ponchos feel like a blanket you can wear, but they somehow look elegant. Add minimal jewelry, a ring or bracelet works perfectly. You’ll feel stylish without even trying.

10. Winter Whites with Cream Leggings

Try cream or off-white leggings for a fresh winter look. Pair them with a chunky white knit sweater and tan ankle boots.

Add a beige trench coat if you’re heading outdoors. A structured handbag ties it all together. Feeling unsure about wearing white?

Don’t overthink it, it looks crisp and seasonally appropriate. This outfit works for everything from coffee dates to holiday shopping trips.

11. Edgy Layers with a Moto Jacket

Pair faux leather leggings with a black moto jacket for an edgy vibe. Wear a plain gray or white tee underneath for balance.

Combat boots or chunky platforms take it up a notch. Carry a crossbody bag to keep your hands free. Heading out? Toss on a plaid scarf for texture.

This look says you’re ready for anything, perfect for concerts or casual nights out with friends.

12. Relaxed Sunday Look with a Shacket

Wear a soft shacket (shirt-jacket hybrid) over your leggings. Choose a neutral tone, like beige or olive green.

Add shearling-lined boots for that warm, wintry feel. A knit hat with a pom-pom adds a playful touch. This outfit screams “cozy Sunday.”

It’s the kind of thing you’d wear to a farmer’s market or a lazy breakfast outing. Keep it simple, yet undeniably you.

13. Cozy Cold Weather Look with Fleece-Lined Leggings

Start with fleece-lined leggings that keep your legs warm. Pair them with a turtleneck sweater and slip on tall boots.

Add a long coat to block out the chill. Don’t forget a knitted scarf and gloves, they’ll make a difference when the wind bites.

This outfit works for outdoor walks or quick errands on cold days. It’s simple, functional, and keeps you cozy while still feeling stylish.

14. Chic Flare Leggings with a Blazer

Pull on black flare leggings for a sleek, balanced look. Pair them with a fitted tank and a long blazer.

Add ankle boots to give the outfit some height. A statement necklace or a simple chain completes the outfit. It’s perfect for casual meetings or grabbing lunch with friends.

The flared cut adds something extra, giving your look movement and a little flair without overdoing it.

15. Work-Ready Outfit with Ponte Leggings

Ponte leggings are thicker, so they work well for office wear. Pair them with a long tunic blouse and loafers. Add a structured blazer for that professional touch.

Need warmth? A wool coat works without looking too casual. This outfit feels polished but still lets you move freely.

It’s perfect for sitting at a desk all day or dashing between meetings. Who said comfort and work can’t go hand in hand?

16. Sleek Pleather Leggings for Nights Out

Pleather leggings are your go-to for dressing up. Pair them with a silky blouse and heeled boots.

A cropped leather jacket adds edge without overwhelming the look. Keep accessories minimal, like a clutch or small earrings.

This outfit works for date nights or drinks with friends. Pleather adds texture and feels like a bold choice. Plus, it pairs well with almost anything.

17. Mid-Length Cardigan for Easy Layers

Wear black leggings with a mid-length cardigan over a tank. Add flat boots or sneakers for a relaxed vibe. Toss on a crossbody bag, and you’re ready to go.

This is the kind of outfit you’d wear for a coffee run or grocery shopping. It feels effortless, like you didn’t try too hard.

The cardigan adds just enough coverage to keep you warm without making you feel bundled up.

18. Cute Winter Outfit with Pastel Colors

Pair pastel-colored leggings with a matching hoodie for a fun look. Add white sneakers and a long, puffy vest to tie it together.

Throw on a beanie in a matching tone for extra warmth. This outfit works for casual outings or even lounging at home.

Pastels feel refreshing during winter, breaking away from darker shades. You’ll feel cozy and playful without sacrificing comfort.

19. Comfy Layers with an Oversized Sweatshirt

An oversized sweatshirt and basic leggings are a match made in heaven. Wear them with shearling-lined boots for extra comfort.

A beanie and fingerless gloves keep you warm while you stay hands-free. It’s the perfect outfit for lazy days or quick errands.

You’ll feel like you’re wrapped in a blanket but still look put-together. Add a mug of hot coffee, and it’s a whole vibe.

20. Monochromatic Look with Gray Tones

Pair gray leggings with a matching gray sweater for a monochrome vibe. Add silver sneakers or neutral ankle boots to complete the look.

A puffer jacket in a darker shade of gray keeps it all cohesive. Monochromatic outfits feel easy and look modern.

It’s great for those days when you don’t want to think too hard about your look but still want to look polished.

21. Athletic Style with Leggings and a Zip-Up Hoodie

Start with leggings and a zip-up hoodie for a sporty look. Add trainers and a lightweight scarf for outdoor activities. A quilted vest works if it’s extra cold.

This outfit is great for running errands or taking a brisk walk. You’ll feel ready for anything, even if you’re just heading to the grocery store.

It’s simple, functional, and makes you feel active without trying too hard.

22. Festive Red Leggings with a Sweater

Pull on red leggings to add a festive touch to your outfit. Pair them with a cream sweater and tall brown boots. Add a plaid scarf for a pop of pattern.

This look feels warm and cheerful, great for holiday gatherings or even family photos. Red leggings might feel bold, but they’re fun to play with during winter.

Try them out and see how they lift your mood.

23. Neutral Tones with Camel and Beige

Pair camel-colored leggings with a beige sweater for a soft look. Add tan ankle boots and a matching crossbody bag.

A trench coat keeps things light but warm enough. This outfit is perfect for casual outings or even a cozy dinner.

Neutral tones feel calm and easy to work with. You’ll look chic without standing out too much, letting the subtle colors do the talking.

24. Edgy Winter Outfit with Dark Layers

Wear dark gray leggings with a black turtleneck for an edgy base. Add combat boots and a cropped moto jacket for extra attitude.

Toss on a knit scarf if you need warmth. This outfit works for concerts, casual dinners, or even late-night strolls.

Dark tones feel bold and grounded, giving your look a little edge without overdoing it. You’ll look effortlessly cool while staying practical for winter.

Must-Have: Plus Size Winter Party Dresses.

➜ Styling Tips for Plus Size Winter Legging Outfits

Let me share my tried-and-true tips for styling winter leggings when you’ve got curves to love.

I’ve learned these through years of dressing my own plus size body and helping others find their confidence.

1. Start with the right foundation: Pick leggings that fit your curves without squeezing.

You want them thick enough that they don’t show through – hold them up to the light to test. High-waisted styles give you support and prevent roll-down during the day.

Remember how we’ve all dealt with that annoying mid-day adjustment? Not anymore!

2. Think about proportions with your layers: When you pair tight leggings with looser tops, you create balance. Try a tunic or sweater that hits at mid-thigh.

This length covers your hips while showing off your legs. I learned this trick after years of wearing tops that were too short or too long.

3. Layer smart, not bulky: Start with your leggings, add a fitted long-sleeve top, then layer a cardigan or sweater.

Each piece should work together without adding extra volume. You know that feeling when you can’t put your arms down? We’re avoiding that!

4. Choose your boots with purpose: Ankle boots elongate your legs when paired with leggings in the same color.

Mid-calf or knee-high boots give you coverage and warmth. Plus, boots with a small heel lift your booty – who doesn’t want that?

5. Add structure with a coat or jacket: A structured coat breaks up the softness of leggings and creates a polished look.

Pick one that ends at your hips or mid-thigh. Trust me, the right coat transforms your whole outfit from “just wearing leggings” to “put together.”

6. Play with textures to add interest: Mix leather leggings with a soft sweater, or velvet leggings with a denim jacket.

Different textures draw the eye where you want it. I once got stopped in the street when I paired faux leather leggings with a chunky knit sweater!

7. Accessorize to tie it all together: A long necklace creates vertical lines that lengthen your body. Scarves add warmth and style without bulk.

Belt a long cardigan to define your waist. These little touches make your outfit feel complete and intentional.

💡 Remember – these aren’t rules set in stone. They’re starting points for you to find what makes you feel amazing. Your body deserves to feel comfortable and look fabulous this winter!

Final Thoughts

Your perfect plus size winter legging outfits are waiting in your closet right now. Yes, right now!

Take another look, those leggings you’ve been nervous about wearing? They’re about to become your best friends this winter.

Remember what we talked about, it’s not about following strict rules. It’s about feeling good in your clothes and expressing yourself.

Think about how amazing it’ll feel to step out in an outfit that makes you smile when you catch your reflection.

I want you to try something. Tomorrow morning, put on those leggings, layer up like we discussed, and watch how your confidence grows.

You might surprise yourself! And when someone asks where you got your outfit idea? Tell them you’ve learned to dress your curves with love.

Fashion should lift you up, not hold you back. Your body deserves to feel comfortable and look amazing this winter. Now go ahead, rock those leggings with pride.