Whether you’re heading to class, running errands, chilling at home, or dressing up for a casual dinner, leggings are the winter wardrobe essential that can be styled a million ways. From fleece-lined pairs that keep you warm to leather-look leggings that bring the edge, this guide is here to help you dress them up, down, or somewhere in between.
In this post, you’ll find 25 stylish winter leggings outfits—perfect for staying cozy and looking like you put in way more effort than you actually did. Let’s get into it.
Oversized Hoodie + Fleece Leggings + Uggs
Cozy up with a pastel oversized hoodie, fleece-lined black leggings, and classic Uggs. Add crew socks peeking out, a messy bun, and a crossbody bag for a comfy, casual winter outfit that’s perfect for school runs, lounging, or grabbing hot cocoa with friends.
2. Long Puffer Coat + Thermal Leggings + Chunky Sneakers
Beat the chill with thermal leggings under a longline puffer. Add a fitted turtleneck, chunky sneakers, and a ribbed beanie. Ideal for commuting, shopping, or outdoor coffee dates when you want warmth without sacrificing style.
3. Faux Leather Leggings + Knit Sweater + Ankle Boots
Add edge with faux leather leggings, a chunky knit sweater, and block-heel ankle boots. Perfect for date nights, brunch, or when you need a fashion-forward look that’s still warm and comfortable. Gold jewelry completes the outfit.
4. Sherpa Jacket + Cropped Hoodie + Leggings
Layer a soft sherpa jacket over a cropped hoodie and black leggings. Pair with platform sneakers or chunky boots. A messy topknot or claw clip adds trendy flair—perfect for Gen Z winter vibes or weekend errands.
5. Blazer + White Tee + Black Leggings
Level up your basics by layering a structured blazer over a white tee and sleek black leggings. Add loafers, a sleek bun, and minimal gold jewelry for a casual-chic winter look that transitions from work to dinner.
6. Matching Legging Set + Wool Coat + Combat Boots
A ribbed or knit legging set under a long wool coat is the ultimate cozy-meets-classy vibe. Combat boots toughen it up, while a mini bag and oversized scarf pull it all together. Wear it to brunch, errands, or casual coffee meetings.
7. Cropped Sweater + High-Waist Leggings + Beanie
Tuck a chunky cropped sweater into high-waisted leggings. Add winter boots, fuzzy socks, and a knit beanie for a warm, effortlessly cute look that’s perfect for hanging out, working from home, or casual winter walks.
8. Turtleneck + Faux Fur Vest + Faux Leather Leggings
Style a sleek turtleneck under a fluffy faux fur vest and faux leather leggings. Add heeled boots and a structured tote for a glam winter look that’s ideal for holiday parties, girls’ nights, or luxe lunches.
9. Puffer Vest + Hoodie + Printed Leggings
Go playful with printed leggings, a cozy hoodie, and a cropped puffer vest. Great for travel days, Target runs, or casual hangouts. Finish with chunky sneakers and a bubble braid or high ponytail.
10. Henley Top + Fleece Leggings + Blanket Scarf
Layer a soft Henley shirt over fleece leggings, then wrap up in a chunky blanket scarf. Add winter boots and a thermal beanie for a functional yet stylish winter fit that’s perfect for road trips or staying warm indoors.
11. Oversized Flannel + Thermal Leggings + Beanie
Mix grunge and cozy by wearing thermal leggings with a longline flannel shirt. Add a simple tee underneath and finish with boots and a cuffed beanie. This low-effort look works well for class, errands, or casual meetups.
12. Graphic Sweatshirt + Leggings + Sherpa-Lined Sneakers
Your favorite band or quote tee sweatshirt pairs perfectly with black leggings. Add sherpa-lined sneakers, slick-back bun, and a tote bag for the ultimate comfy streetwear winter fit.
13. Cardigan + Crop Top + Leggings
Go for a layered lounge look with a long cardigan, fitted crop top, and high-rise leggings. Finish with slippers or slides indoors—or sneakers outside. Add gold hoops and lip gloss for a simple yet chic vibe.
14. Down Jacket + Hoodie Dress + Leggings
Throw a hoodie dress over leggings and layer with a cropped down jacket for cozy, layered perfection. Add over-the-knee boots and a headband for a cute winter look that’s ideal for a day in the city.
15. Mock Neck Top + Corduroy Shacket + Ribbed Leggings
This textural look pairs a ribbed legging with a mock neck top and a corduroy shacket. Style with lug boots and a structured bag for a soft utility aesthetic. Great for school or a weekend lunch date.
16. Knit Tunic + Leggings + Over-the-Knee Boots
Pair an oversized knit tunic with high-rise leggings and tall suede boots. Add a belt at the waist for shape. This outfit is cozy yet elevated—perfect for brunch, church, or date night during cold months.
17. Cropped Puffer + Leggings + Chunky Scarf
A cropped puffer layered over leggings and paired with a thick knit scarf creates the ultimate winter baddie look. Add lace-up boots and statement earrings. Ideal for quick coffee runs or social media selfies.
18. Sweatshirt + Quilted Vest + Colorful Leggings
Switch things up with colorful or tie-dye leggings. Style them with a neutral sweatshirt and quilted vest. Add winter boots and minimal makeup for a fresh, casual look that works all season long.
19. Blazer Coat + Turtleneck Bodysuit + Faux Leather Leggings
Go sleek with a blazer-style coat over a fitted turtleneck bodysuit and faux leather leggings. Add heeled boots and a top-handle bag. A perfect look for meetings, dates, or downtown winter days.
20. Cropped Hoodie + Matching Leggings + Beanie
Go monochrome with a cropped hoodie and matching leggings set. Pair with a beanie, white sneakers, and a mini backpack. This look is cozy enough for indoors but cute enough to wear out on casual days.
21. Crewneck Sweater + Scarf + Knit Leggings
Knit leggings and a crewneck sweater are a cold-weather dream combo. Add a blanket scarf and Chelsea boots. Perfect for reading at cafés or walking in the snow while staying cute and warm.
22. Thermal Bodysuit + Teddy Coat + Black Leggings
Stay snug in a thermal bodysuit layered under a plush teddy coat and basic black leggings. Add ankle boots and a statement bag for a cozy yet Instagram-worthy look.
23. Puffer Coat + Cropped Knit Top + Patterned Leggings
Brighten up gloomy days with patterned or neon leggings. Pair with a cropped knit top and oversized puffer. Add snow boots and clear glasses for a bold, sporty winter vibe.
24. Sherpa Pullover + Leggings + Winter Boots
This outfit screams cozy: a sherpa pullover with black leggings and snow boots. Top with a pom-pom beanie and puffer tote for a go-to snow day or firepit look with major comfort points.
25. Fluffy Jacket + Graphic Tee + Moto Leggings
Edgy and soft meet in this combo: a fluffy cropped jacket, fun graphic tee, and moto-style leggings. Add combat boots, a high ponytail, and a statement lip for a cool-girl winter vibe.
Conclusion
From cozy basics to elevated streetwear, leggings outfits in winter are far from boring—they’re versatile, comfy, and totally customizable. Whether you’re dressing up or down, there’s a legging look here that fits your vibe.
