Leggings in winter? Absolutely! Gone are the days when these comfy stretchy pants were just for the gym. Now, they’re a versatile staple that can take you from cozy nights in to stylish nights out.
As someone who practically lives in leggings during the colder months, I’ve teamed up with some fashion-forward friends to bring you 15 chic ways to rock your leggings this winter. Whether you’re running errands, cozying up with a cup of cocoa, or stepping out for a night on the town, your legs (and your style cred) will thank you.
Winter leggings style isn’t just about comfort—it’s about mixing textures, layering intelligently, and letting your personality shine through every outfit. So grab a warm blanket (or your favorite oversized hoodie), and let’s dive into these looks that will keep you warm, stylish, and totally unstoppable.
Oversized Sweater and Ankle Boots
Who says comfort can’t be chic? Pair your favorite leggings with an oversized sweater that’s basically a wearable hug.
Add some ankle boots, and suddenly your winter outfit goes from “I just rolled out of bed” to “I woke up like this—flawless.” Play with textures: a cable-knit or chunky wool sweater adds depth and keeps the outfit from looking flat.
Throw on a scarf or statement earrings, and this ensemble works for coffee runs, casual workdays, or strolling around the city. Cozy, chic, and effortlessly you.
Leather Jacket and Combat Boots
Channel your inner rock star with this edgy winter combo. Black leggings, a crisp white tee, and a leather jacket = instant cool.
Add combat boots, and you’re ready to face the world—or maybe start a punk band. Studded accessories take the look to the next level, but don’t go overboard; we’re aiming for effortless badassery, not setting off metal detectors.
This outfit is perfect for city walks, casual nights out, or anytime you want to add a little attitude to your wardrobe. Confidence is your best accessory here.
Tunic Dress and Knee-High Boots
Long live the leggings-as-pants debate! A flowy tunic dress over leggings cleverly sidesteps the issue, giving you a comfortable yet stylish outfit.
Pair with knee-high boots for the ultimate autumn/winter vibe. This combo works wonders on days when you’ve indulged a little too much at Thanksgiving (not that I’m speaking from experience or anything…).
The tunic dress adds elegance, while the leggings keep you warm—so you’re both cozy and polished. Perfect for casual meet-ups or weekend brunches.
Plaid Shirt and Sneakers
Embrace your inner lumberjack (fashion edition) with an oversized plaid shirt layered over leggings.
Slip into some comfy sneakers, and you’re ready for everything from weekend hikes to Netflix marathons. Top it off with a beanie for extra warmth and a casual-cool vibe.
This outfit is perfect for cozy-casual days when you want effortless style that still feels intentional. Layering is key here—it’s about balancing comfort, warmth, and aesthetics.
Faux Fur Vest and Riding Boots
Who says you can’t be glamorous AND practical? A faux fur vest over leggings instantly elevates your winter outfit.
Pair with riding boots to keep the look grounded (literally) while adding a touch of luxury. Perfect for photoshoots, holiday markets, or “let’s go cut down our own Christmas tree” adventures.
The faux fur adds texture and drama, while the boots keep your look grounded, making it chic, playful, and winter-ready.
Denim Shirt and Loafers
Sometimes, simple is best. A classic denim shirt over black leggings is the wardrobe equivalent of PB&J—it just works.
Add loafers for a preppy twist, and you’re ready for a day of errands, study sessions, or casual lunch dates. The charm of this outfit is in its simplicity; it’s polished without trying too hard.
Layering a scarf or adding a statement bag instantly transforms it from basic to effortlessly stylish.
Chunky Cardigan and Moccasins
If “hygge” were an outfit, this would be it. Wrap yourself in a chunky cardigan, slide into cozy moccasins, and suddenly every day feels like a warm hug.
Perfect for lounging, working from home, or even casual errands. Add a knit hat or blanket scarf for extra winter vibes. Even if adulting calls, this look makes it look like you’ve got everything under control.
Long Blazer and Heeled Ankle Boots
Who says leggings can’t be office-appropriate? Pair them with a crisp blouse, a long blazer, and heeled ankle boots for instant boss-lady energy.
This look works for meetings, presentations, or when you want to exude sophistication with minimal effort. It’s sleek, polished, and commands attention without feeling stiff.
Poncho and Wedge Boots
Channel your inner boho goddess with a colorful poncho layered over leggings.
Wedge boots add a touch of height while remaining practical and comfortable. Perfect for casual outings, coffee dates, or winter errands where you want to stand out without compromising ease.
The poncho adds drama and personality, turning a simple leggings outfit into a style statement.
Turtleneck and Over-the-Knee Boots
Channel classic elegance with a fitted turtleneck tucked into leggings, then layer on over-the-knee boots for instant sophistication.
Whether heading to brunch, a gallery, or just the grocery store runway, this combo is effortlessly chic. Confidence is key: walk tall, shoulders back, and strut like you own the pavement.
Flannel Shirt and Ugg Boots
The ultimate in cozy-casual winter style: pair a soft flannel shirt with leggings and throw on Ugg boots.
This look is perfect for pumpkin spice lattes, hayrides, or Netflix marathons. Bonus: it’s warm, comfy, and doesn’t compromise on style. Perfectly “basic” but with undeniable charm.
Sweater Dress and Thigh-High Socks
Want to feel cozy AND stylish? Layer a sweater dress over leggings, add thigh-high socks, and finish with ankle boots.
It’s like wearing a blanket but make it fashion. The socks act as leg warmers for adults—warm, stylish, and effortlessly cute. Great for casual outings, school runs, or chilly winter nights.
Puffer Vest and Snow Boots
Leggings + thermal shirt + puffer vest = winter-ready perfection.
Add snow boots, and you’re ready for snowball fights, building snowmen, or spontaneous snow angel sessions. Practical, stylish, and totally Instagram-worthy, this outfit balances warmth and street-style vibes.
Belted Tunic and Ballet Flats
When you want a polished look without “real” pants, a belted tunic over leggings is your go-to.
Pair with ballet flats for elegance, and you’ve got an outfit perfect for art galleries, coffee dates, or casual work meetings. It’s flattering, chic, and makes minimal effort look intentional.
Hoodie and High-Top Sneakers
Sometimes, you just need to channel your inner teenager. Pair an oversized hoodie with leggings and high-top sneakers for the ultimate comfy-cool look.
Perfect for skate parks, weekend lounging, or casual walks. Easy, playful, and effortlessly stylish—it’s all about confidence and attitude here.
