15 Winter Outfits With Legging

Winter is here, and I know how tricky it can be to stay warm while looking stylish. That’s why I love leggings—they’re versatile, comfy, and pair well with almost anything. Whether you’re running errands, meeting friends, or just lounging at home, I’ve found that the right outfit with leggings can keep you cozy and chic all season long. You’ll see how easy it is to mix and match pieces to create looks that suit your vibe.

In this article, I’m excited to share 15 winter outfit ideas featuring leggings that you can try this season. From casual to polished, these combinations are perfect for keeping you comfortable and on-trend during chilly days. I hope you find something that inspires you to make the most of your winter wardrobe. Let’s dive into these fabulous outfit ideas together!

My Winter Outfit Ideas with Leggings

Oversized Sweater with Fleece-Lined Leggings

When it’s chilly outside, I always reach for my cozy oversized sweater and pair it with fleece-lined leggings. It’s the kind of outfit that keeps you warm without making you feel bulky. You’ll love how effortlessly stylish it looks while giving you that snug and comfy vibe for winter days.

Puffer Jacket with Thermal Leggings

I think we all need an outfit that’s as functional as it is fashionable, and this combo nails it. A puffer jacket with thermal leggings keeps you insulated from the cold while making you look on point. You’ll appreciate how easy it is to layer and stay toasty during those frosty mornings.

Long Cardigan with Leather Leggings

Whenever I want to blend comfort with a little edge, I go for a long cardigan and leather leggings. It’s the perfect mix of cozy and chic, and you can wear it anywhere, from brunch to a casual day out. You’ll find it so easy to style with boots or sneakers.

Turtleneck Sweater with High-Waisted Leggings

I love how a turtleneck sweater instantly makes any outfit look classy, especially when paired with high-waisted leggings. It’s such a simple yet polished look that you’ll feel confident wearing it all day. Add your favorite accessories, and you’re ready for anything.

Chunky Knit with Printed Leggings

If you’re like me and love patterns, you’ll adore how printed leggings pop under a chunky knit sweater. It’s a fun way to show your personality while staying warm. You can switch it up with different prints, and I promise, you’ll never get bored of this look.

Wool Coat with Black Leggings

This pairing is my go-to for when I want to look elegant yet stay comfortable. A wool coat with black leggings creates such a timeless and sophisticated outfit. You’ll feel warm and chic whether you’re heading to work or meeting friends.

Plaid Shirt with Stretchy Leggings

A plaid shirt with stretchy leggings is one of those outfits I can throw on and feel instantly put together. It’s relaxed but still stylish enough for running errands or a coffee date. You’ll love how versatile and comfy this combo is.

Faux Fur Vest with Ribbed Leggings

I always feel extra cozy and stylish when I wear a faux fur vest with ribbed leggings. The textures make the outfit interesting, and you’ll love how effortlessly fashionable it feels. It’s great for layering on those colder days.

Hoodie with Glossy Leggings

This look is all about blending casual and trendy vibes. A hoodie with glossy leggings is my pick when I want to keep it simple yet fashionable. You’ll appreciate how the glossy finish adds a bit of flair to your everyday winter style.

Shacket with Patterned Leggings

I think a shacket and patterned leggings are a match made in heaven. The shacket adds warmth while the leggings bring in some fun prints. You’ll enjoy how playful and cozy this combo feels for winter outings.

Down Vest with Workout Leggings

For those active winter days, I rely on a down vest and workout leggings. It’s lightweight yet warm, making it perfect for walks or errands. You’ll love how sporty and practical this outfit is without compromising on comfort.

Peacoat with Stirrup Leggings

I find this combo so polished and winter-appropriate. A peacoat paired with stirrup leggings is ideal when you want to feel sophisticated yet comfortable. You’ll feel like you’re ready for any occasion with this effortlessly chic look.

Sweater Dress with Leggings

Whenever I want to feel a little dressier, I go for a sweater dress with leggings. It’s cozy and stylish, and you’ll love how easy it is to wear for any event. Just add your favorite boots, and you’re good to go.

Trench Coat with Slim-Fit Leggings

A trench coat with slim-fit leggings is a winter classic that I always turn to. It’s sleek and keeps you warm without looking too heavy. You’ll love how this outfit gives you a polished look for any winter day.

Flannel Tunic with Jeggings

I think nothing feels more laid-back and cozy than a flannel tunic with jeggings. It’s the kind of outfit you can relax in but still look stylish. You’ll love how this combo works for casual winter days or staying warm at home.