Let’s be honest, when the temperature drops, all we really want is to be comfortable without sacrificing our style. And nothing says comfort quite like a trusty pair of leggings. But if you’ve ever wondered how to wear leggings in the winter without just looking like you’re headed to the gym, you’re in the right place.
The secret is in the styling. The right layers, shoes, and accessories can transform your favorite leggings from loungewear into a legitimate, fashionable winter outfit. This guide is here to banish that winter style fatigue.
We’re breaking down 30 real-life, easy-to-recreate winter outfits with leggings that are as practical as they are chic. From running errands on a frosty morning to a cozy date night, we’ve got you covered. Get ready to fall in love with your leggings all over again.
Casual & Weekend Errands
Your go-to outfits for coffee runs, grocery shopping, or a casual walk. These looks prioritize ultimate comfort and easy, throw-on style.
1. Grey Beanie + Grey Hoodie + Black Puffer Vest + Purple Leggings + Tan Ugg Boots
Description: This outfit is the definition of cozy casual. A grey hoodie and beanie create a soft base, while a black puffer vest adds warmth without arm bulk. Purple leggings add a fun pop of color, and tan Ugg boots complete the comfortable vibe.
Why It Works: The vest traps heat close to your body while allowing for easy movement. The monochromatic top (grey) lets the colorful leggings shine without overwhelming the look.
Pro Tip: Don’t be afraid of color. If purple isn’t your thing, try leggings in burgundy, forest green, or a fun pattern to make a simple outfit more interesting.
2. Grey Pom-Pom Beanie + Red Puffer Jacket + Blue Geometric Leggings + Hiking Boots + Orange Backpack
Description: Perfect for a winter hike or a day exploring the city. A bright red puffer jacket ensures you’re visible and warm. Patterned blue geometric leggings add personality, and sturdy hiking boots provide grip and ankle support.
Why It Works: This outfit is all about function meeting fashion. The technical fabrics are built for activity, and the bright colors are cheerful against a grey winter landscape.
Pro Tip: For active days, choose moisture-wicking leggings. They will keep you dry and comfortable, whether you’re working out or just moving around a lot.
3. Black Beanie + Pink Fleece Pullover + Grey Leggings + Brown Hiking Boots
Description: A sweet and sporty look that’s incredibly easy to wear. A soft pink fleece pullover is both warm and cute. It’s paired with simple grey leggings and practical brown hiking boots for a grounded, outdoorsy feel.
Why It Works: Fleece is a fantastic insulator that’s lightweight. The combination of pink and brown is unexpectedly charming and feminine.
Pro Tip: Tuck the front of your pullover into the waistband of your leggings just slightly. This small trick defines your waist and prevents a boxy silhouette.
4. White Beanie + Pink Fleece Jacket + Black Leggings + Brown Lace-Up Winter Boots
Description: This outfit offers a slightly more structured take on fleece. A zip-up pink fleece jacket layered over a simple top is a classic. Black leggings are slimming, and rugged brown winter boots handle any slush or snow.
Why It Works: The zip-up jacket allows for better temperature control than a pullover. The white beanie adds a fresh, crisp contrast to the warm pink and black.
Pro Tip: Look for fleece jackets with interesting details like a contrasting zipper or textured fabric to elevate your casual look.
5. Black Beanie + Beige Puffer Jacket + Cream Sweater + Black Leggings + Black Fur-Trim Boots + Black Tote Bag
Description: A chic and neutral outfit for a day of shopping or brunch with friends. A beige puffer jacket over a cream sweater feels luxurious and warm. Black leggings and fur-trim boots keep the look streamlined and sophisticated.
Why It Works: The tonal beige-and-cream combination on top is very trendy and flattering. The black beanie and boots tie together neatly with the leggings.
Pro Tip: When wearing light colors on top, dark leggings on the bottom help to balance the outfit and create a slimming effect.
6. Grey Beanie + Grey Turtleneck Sweater + Plaid Long Coat + Black Skinny Pants + Chunky Sneakers
Description: A masterclass in layering for a cold day. A grey turtleneck and leggings form a warm base layer. A long plaid coat thrown over the top adds major style points and extra insulation. Chunky sneakers keep it modern.
Why It Works: The long coat is key for keeping your legs extra warm. The plaid pattern adds visual interest to an otherwise simple outfit.
Pro Tip: Your base layer (turtleneck and leggings) should be form-fitting so your outer layers don’t add unnecessary bulk.
7. Black Beanie + Grey Shearling Jacket + Red Hoodie + Black Skinny Jeans + White Sneakers + Black Scarf
Description: This outfit has a cool, urban vibe. A cozy grey shearling jacket is layered over a pop-of-color red hoodie. Black skinny jeans (a close cousin to leggings) and white sneakers keep the look sharp and comfortable.
Why It Works: The shearling provides incredible warmth and texture. The red hoodie peeking out adds a youthful and energetic touch.
Pro Tip: A hoodie is a secret weapon for adding casual warmth under almost any jacket. Just make sure your jacket is slightly oversized to accommodate the extra layer.
8. Black Beanie + Black Coat + Grey Leggings + White Nike Sneakers + Black Tote Bag
Description: An athleisure look that is perfect for running errands. A long black coat elevates simple grey leggings and white sneakers instantly. A black beanie and tote bag pull the monochromatic elements together.
Why It Works: The long, tailored coat makes the sporty elements underneath look intentional and chic. It’s a quick outfit that looks like you put in much more effort.
Pro Tip: The key to nailing athleisure is to keep your pieces clean and sleek. Avoid overly worn-out sneakers or leggings to maintain a polished look.
9. Black Zip Hoodie + Green Patterned Leggings + White Sneakers
Description: A simple, no-fuss outfit that still has personality. A basic black zip-up hoodie is the perfect companion for statement leggings. Here, green patterned leggings become the focal point, while white sneakers keep it fresh.
Why It Works: It’s an easy formula: a neutral top + fun leggings = a done outfit. This is a great way to express your style with minimal effort.
Pro Tip: Let your leggings do the talking. If they have a busy pattern, keep everything else simple and solid-colored to avoid a clashed look.
Cozy & At-Home Style
For those days when you’re working from home or simply enjoying a relaxing day indoors. Maximum comfort is the goal.
10. Beige Oversized Half-Zip Sweater + Black Polka Dot Tights + White Fuzzy Slippers + Teddy Bear Hat
Description: The ultimate cozy, at-home outfit that’s too cute not to share. An oversized beige half-zip sweater is like wearing a blanket. Fun polka dot tights and a playful teddy bear hat add a whimsical touch.
Why It Works: This is pure comfort. The oversized sweater allows for easy movement, and the fun accessories boost your mood on a lazy day.
Pro Tip: Invest in high-quality, non-see-through leggings or tights specifically for lounging. They feel more luxurious and will last longer.
11. White Fuzzy Sweater + Black Leggings + White Knit Slippers
Description: A simple and incredibly soft monochromatic loungewear set. A plush white fuzzy sweater pairs perfectly with classic black leggings. Coordinating white knit slippers complete the cozy ensemble.
Why It Works: The contrast between the fluffy white sweater and sleek black leggings is visually appealing and comfortable. It’s an effortless outfit for a slow morning.
Pro Tip: To avoid shedding from fuzzy sweaters, pop them in the freezer for a few hours before wearing them for the first time.
12. Camel Scarf + Black Ribbed Long-Sleeve Top + Black Leggings + Tan Ugg Boots
Description: This is the perfect “I need to quickly run outside to get the mail” outfit. A warm black long-sleeve top and leggings are your base. A chunky camel scarf adds a burst of warmth and style, while Ugg boots slide on easily.
Why It Works: The scarf is the hero here, easily transforming basic loungewear into a presentable outfit for a quick trip outdoors.
Pro Tip: Choose a large, blanket-style scarf. You can wear it loosely or wrap it tightly for extra warmth when you step outside.
Dressed Up & Date Night
Who says you can’t wear leggings for a nicer occasion? These outfits show how to elevate them for a dinner or a night out.
13. Black Coat + Black Mini Dress + Black Tights + Plaid Blanket Scarf + Black Ankle Boots
Description: A classic winter outfit that’s effortlessly chic. A little black dress layered over black opaque tights (or leggings) is a foolproof base. A plaid blanket scarf adds pattern and warmth, and a long black coat finishes the look.
Why It Works: This is a timeless formula. The monochromatic base is slimming, and the scarf provides a stylish pop of pattern.
Pro Tip: For a seamless look, choose footed leggings or tights and pair them with boots. This creates a long, continuous line.
14. Camel Coat (draped) + Black Sleeveless Turtleneck Crop + Burgundy Skinny Pants + Black Ankle Boots
Description: A sophisticated and modern outfit. Burgundy skinny pants (or faux-leather leggings) add a rich color and texture. A black sleeveless turtleneck keeps the top half sleek, and a camel coat draped over the shoulders adds instant polish.
Why It Works: The draped coat is a power move that looks incredibly fashionable. The outfit balances skin (arms) with coverage for a dynamic look.
Pro Tip: This look works best for going from a warm car to a restaurant. The sleeveless top keeps you comfortable indoors while the coat handles the cold outside.
15. Black Leather Jacket + White Sweater Dress + Black Leggings + Black Ankle Boots
Description: A cool and balanced outfit for a casual date night. A sweet white sweater dress is toughened up with a black leather jacket. Black leggings and ankle boots extend the edgy vibe and keep you warm.
Why It Works: The mix of feminine (dress) and masculine (jacket) elements is always stylish. The leggings make the shorter dress winter-appropriate.
Pro Tip: Make sure your leggings are completely opaque for a dressed-up look. Sheer leggings can cheapen an otherwise chic outfit.
16. Beige Sequin Textured Jacket + Black Scarf + Tan Mini Skirt + Sheer Tights + Black Over-the-Knee Boots
Description: A glamorous and festive outfit. A textured beige jacket that mimics sequins catches the light beautifully. It’s worn over a mini skirt and sheer tights, with stunning over-the-knee boots adding drama and warmth.
Why It Works: The boots are the star, acting as both a statement piece and a practical layer that replaces pants. The outfit is perfect for a holiday party.
Pro Tip: For maximum warmth, wear opaque thermal tights underneath sheer ones. You get the delicate look with the functionality of leggings.
17. Black Oversized Leather Jacket + Black Mini Dress + Black Tights + Black Chelsea Boots + Black Quilted Chanel Bag
Description: An all-black, rock-and-roll ensemble that exudes confidence. An oversized leather jacket adds attitude to a simple black dress and tights. Chunky Chelsea boots and a designer bag add a touch of luxury.
Why It Works: All-black outfits are slimming and chic. The different textures leather, knit, metal, prevent it from looking flat.
Pro Tip: Use accessories to break up the black. A statement bag, a metallic belt, or even a bold lipstick can add the necessary contrast.
18. Plaid Oversized Blazer + Nude Ombre Thermal Tights + Black Mini Shorts
Description: A fashion-forward and edgy look for a trendy event. An oversized plaid blazer is worn as a dress, layered over thermal tights and mini shorts. The nude ombre tights create a unique, leg-lengthening effect.
Why It Works: This is a high-style outfit that plays with proportions. The blazer does the heavy lifting, making it a simple yet impactful look.
Pro Tip: This look is bold. Keep your hair and makeup sleek to let the outfit be the main focus.
Work & Smart-Casual
Yes, you can wear leggings to work! The key is to balance them with structured, professional pieces.
19. Black Blazer & Beige Knit + Black Opaque Leggings + White Dad Sneakers
Description: A perfect smart-casual outfit for a creative workplace. A tailored black blazer and a beige knit top instantly polish up black opaque leggings. Classic white “dad” sneakers add a comfortable and modern touch.
Why It Works: The blazer adds structure and professionalism, making the leggings look intentional. The sneakers keep it from being too formal.
Pro Tip: The leggings must be thick, high-quality, and completely opaque like ponte knit leggings to pass in a work setting.
20. Mustard Fur-Collar Coat + Black Leggings + Black Suede Ankle Boots
Description: A chic and easy outfit for the office commute. A stunning mustard-colored coat with a fur collar makes a bold statement. Underneath, simple black leggings and ankle boots create a sleek, streamlined silhouette.
Why It Works: The coat is the focus, so the simple leggings and boots act as a neutral canvas. This is an easy way to look put together with minimal effort.
Pro Tip: When your outerwear is a statement, keep everything else simple. A structured tote bag would complete this professional look.
21. Belted Cream Sweater + Black Leggings + Black Ankle Boots
Description: An elegant and simple outfit that works for almost any setting. A luxurious, chunky cream sweater is belted at the waist to create shape. Paired with black leggings and boots, it’s a study in timeless style.
Why It Works: The belt is the key detail here. It defines your waist, preventing the oversized sweater from looking sloppy with leggings.
Pro Tip: Choose a belt in a complementary neutral color, like tan or black, to maintain the cohesive, elegant color palette.
22. Burgundy Wrap Coat + Taupe Ribbed Top + Olive Flared Pants
Description: This outfit shows how to style leggings-adjacent pieces. Olive flared pants offer a similar comfort level with a different silhouette. A rich burgundy wrap coat and a taupe ribbed top create a sophisticated, autumnal color story.
Why It Works: The wrap coat is incredibly flattering and stylish. The outfit demonstrates how to build a winter look around comfortable, non-jean bottoms.
Pro Tip: Flared pants are a great alternative to leggings. They allow you to wear warm, thermal leggings underneath completely hidden from view.
23. Camel Long Coat + White Shirt & Black Mini Skirt + Sheer Leggings + Black Knee-High Boots
Description: A classic and preppy office-ready ensemble. A crisp white shirt and black mini skirt create a timeless base. The camel coat adds sophistication, and the knee-high boots function as a warm, stylish alternative to pants.
Why It Works: The knee-high boots essentially act like leggings, providing coverage and warmth. This is a very polished way to wear a skirt in winter.
Pro Tip: For a full-legging alternative, wear black opaque tights or leggings under the skirt and boots for an extra layer of insulation.
Trendy & Fashion-Forward
For those who love to experiment with textures, silhouettes, and the latest trends.
24. Grey Ombre Cardigan + Black Graphic Tee + Black Skinny Pants + Black Winter Boots
Description: A cozy yet cool outfit with a touch of boho flair. A long, grey ombre cardigan adds drama and movement over a simple graphic tee and black leggings. Practical black winter boots keep your feet warm and grounded.
Why It Works: The long cardigan provides extra coverage and warmth for your legs, making it a great layering piece. The graphic tee adds a personal touch.
Pro Tip: Long cardigans can overwhelm a petite frame. Choose one that hits at mid-calf rather than the floor to avoid being swallowed up by fabric.
25. Oversized Grey Knit + Black Faux-Leather Leggings + Black Chelsea Boots
Description: This outfit is a masterclass in mixing textures. A slouchy, soft grey sweater contrasts beautifully with sleek, shiny faux-leather leggings. Black Chelsea boots continue the edgy, modern vibe.
Why It Works: The combination of a cozy knit and cool leather creates a balanced, interesting look. It’s comfortable but undeniably chic.
Pro Tip: Faux-leather leggings are a winter wardrobe hero. They block the wind better than regular leggings and instantly elevate any outfit.
26. Red Plaid Shirt Dress + Black Tights & Faux-Fur Vest + Black Winter Boots
Description: A rustic, festive outfit perfect for a weekend getaway. A red plaid shirt dress is layered over black tights for warmth. A faux-fur vest adds a luxurious texture, and sturdy boots make it practical for outdoor activities.
Why It Works: The vest and boots transform the dress into a winter-appropriate outfit. The plaid pattern is inherently cozy and seasonal.
Pro Tip: Belt the dress over the vest to define your waist and create a more put-together silhouette.
27. White Beanie & Crop Top + White High-Waist Pants + Grey Winter Boots
Description: A bold and sporty look for the fashion-forward. A white beanie and crop top create a bright, eye-catching combination. High-waisted white pants and chunky grey boots balance the look with a utilitarian feel.
Why It Works: This is a high-style, high-contrast outfit. It’s perfect for someone who loves to make a statement and isn’t afraid of light colors in winter.
Pro Tip: This look is best for milder winter days or for being mostly indoors. Layer a warm coat over top when you’re outside.
28. Grey Beanie + Burgundy Zip-Up Jacket + Blue Hiking Pants + Hiking Boots + Grey Backpack
29. Black Puffer Vest + White Long-Sleeve Tee + Black Leggings + Black Fuzzy Boots
30. Grey Hoodie + Black Leggings + White Sneakers
Conclusion
As you can see, leggings are so much more than just gym wear. They are a versatile foundation for countless warm, stylish, and comfortable winter outfits. The key is to think of them as a base layer and build upon them with intention. Use long tops, sweaters, and jackets to create interesting silhouettes. Don’t forget the power of accessories like scarves, hats, and especially your footwear to define the vibe of your outfit.
Whether you’re leaning into cozy casual or dressing up for a night out, your leggings can be your winter style secret weapon. So, open your closet and start experimenting. Which of these 30 winter outfits with leggings are you most excited to try first? Let me know in the comments below!
Frequently Asked Questions (FAQs)
What type of leggings are best for winter?
Look for leggings made from thicker, warmer materials. Ponte knit, fleece-lined, and wool-blend leggings are excellent choices. For outdoor activities, moisture-wicking thermal leggings are ideal. Always ensure they are opaque.
How can I make sure my outfit doesn’t look too casual?
Balance is key. Pair your leggings with more structured or sophisticated pieces like a blazer, a long coat, a tailored tunic, or leather boots. Avoid wearing them with gym-style sweatshirts if you’re aiming for a dressier look.
Can I wear leggings to the office?
In many modern, business-casual environments, yes. The key is to treat them like you would dress pants. Choose high-quality, opaque leggings in a dark color and pair them with a long blazer, a nice sweater, and elegant boots or loafers.
How do I stay warm in leggings when it’s very cold?
Layering is your best friend. Start with a thin thermal base layer, like silk or synthetic long underwear, underneath your leggings. You can also look for specifically designed thermal or fleece-lined leggings for maximum insulation.
What are the best shoes to wear with leggings in winter?
It depends on the outfit. Ankle boots and knee-high boots are classic choices. Chunky sneakers work for a casual vibe, while sleek boots or even loafers can dress them up. The goal is to choose a shoe that complements the top half of your outfit.
