20 Chic Leggings Outfits For Winter That’ll Keep You Warm And Stylish All Season Long

Winter dressing shouldn’t mean choosing between freezing in your favorite jeans or hiding in bulky sweatpants. Yet every year, the same problem comes back: your legs are cold, your cute outfits don’t feel practical, and you end up repeating the same boring winter looks again and again.

Leggings can quietly solve all of that.

When you style them the right way, leggings stop looking like basic gym wear and start feeling like part of a real outfit. With smart layers, good proportions, and cozy textures, they can work for coffee runs, errands, casual days, and even nicer plans.

Below are winter leggings outfit ideas that keep you warm, comfortable, and stylish all season long.

Cozy Cropped Sweatshirt And Black Leggings

This look pairs an oversized cropped sweatshirt with simple black leggings. The cropped shape on top and the high waist on the leggings balance each other out, making your legs look longer.

Add white sneakers to keep things sporty and relaxed. This is perfect for running errands, going to the gym, or just staying comfy on a casual day. The soft color of the sweatshirt adds a gentle touch without being too loud, and it layers easily under a coat when you head outside.

Black Leggings With Puffed Jacket And Scarf

Here, black leggings are styled with a quilted puffer jacket and a big, cozy scarf. The leggings keep your base sleek, while the jacket and scarf add volume and warmth.

A crossbody bag and simple shoes complete the look, making it practical for busy days out. The result is warm, comfortable, and still neat enough for grabbing lunch, shopping, or walking around town on chilly days.

Monochrome Casual With Sporty Sneakers

This outfit uses black leggings with an oversized cream or white sweatshirt for an easy black-and-white look. The sweatshirt feels cozy and relaxed, while the leggings keep your shape streamlined.

Platform or chunky white sneakers give the outfit a sporty feel. It’s ideal for casual outings, meeting friends, or staying comfortable at home while still feeling put together.

Cozy Sweatshirt With Burgundy Leggings

A soft grey sweatshirt paired with burgundy leggings makes a simple winter outfit feel a bit more special. The neutral top keeps things calm, while the rich color of the leggings adds depth.

White sneakers keep the look clean and fresh. This combo is perfect for low-key weekends, coffee dates, or days when you want something comfy that still looks like you tried.

Cozy Cream Sweatshirt And Black Leggings

This pairing is a true winter classic: a cream oversized sweatshirt with black leggings. The contrast between light on top and dark on the bottom is flattering and easy to style.

Add socks and minimal sneakers, and you’re done. You can also throw on a crossbody bag if you’re heading out. This outfit works for errands, relaxed work-from-home days, or any casual plan when you want warmth with very little effort.

Oversized Hoodie And Black Leggings

This look is all about comfort: black leggings with an oversized hoodie in a neutral shade like beige or tan. The hoodie keeps you warm and cozy, and the leggings keep the shape from looking too bulky.

White sneakers finish the look and add a bit of brightness. It’s the kind of outfit you reach for again and again on cold mornings when you want something easy, warm, and still presentable.

Striped Top With Flare Leggings

Here, navy or dark flare leggings are styled with a striped button-up shirt. The shirt brings a classic, slightly dressy feel, while the flared leggings give a longer, more balanced line.

Sneakers keep the outfit casual and comfortable. This look is great for casual office settings, weekend plans, or days when you want something a step above a basic sweatshirt-and-leggings combo.

Houndstooth Jacket With Black Leggings

This outfit dresses leggings up with a cropped houndstooth jacket. The pattern and structure of the jacket instantly make the leggings look more polished.

Wear it with simple shoes or boots and a small handbag. It’s a great option for dinner, casual meetings, or anytime you want to feel a bit more put together while still enjoying the comfort of leggings.

Striped Sweater With Classic Black Leggings

A striped turtleneck or high-neck sweater and black leggings make a warm, easy winter outfit. The sweater adds volume and interest on top, while the leggings keep the look clean and fitted.

Pair it with flats or boots, depending on the weather. This outfit works well for brunch, casual office days, or running around town when you want to be both cozy and stylish.

Black Leggings With Cream Cardigan Layers

This look builds on a simple base: black leggings and a black top, layered with a long cream cardigan on top. The leggings give you a smooth, warm base, and the cardigan adds movement and texture.

Add ankle boots and simple jewelry to complete the outfit. It’s perfect for days when you need something that can go from daytime errands to a casual dinner without changing.

Burgundy Cardigan With Black Leggings

Here, black leggings are styled with a burgundy cardigan for a rich, winter-ready outfit. The leggings keep everything sleek, while the cardigan adds color and warmth.

Knee-high boots and a small shoulder bag make the look feel finished and intentional. This combination works for daytime plans, evening outings, or just feeling a little more dressed up in the cold.

Camel Vest With Tan Leggings

This neutral outfit mixes tan leggings with a white top and a camel vest. The leggings fit close to the body and keep you warm, while the vest adds structure and a bit of extra insulation.

White sneakers and simple accessories keep things clean. It’s a great option for casual outings, coffee runs, or shopping days, especially if you like soft, earthy tones in winter.

Cream Blazer With Chocolate Flare Leggings

Here, flare leggings in a deep brown shade are paired with a cream blazer. The blazer adds polish and warmth, and the flared leggings give the outfit a modern twist.

White sneakers keep the look relaxed but still neat. This combo works nicely for casual offices, lunch dates, or more polished daytime plans where you still want to feel comfortable.

Black Flare Leggings With Puffer Jacket

This look uses all-black pieces: black flare leggings and a black puffer jacket. The flares lengthen your legs, while the puffer jacket keeps you toasty and adds volume on top.

A simple top underneath and white sneakers for contrast finish the outfit. It’s a strong, easy look for cold days, giving you warmth and a bit of edge at the same time.

Black Leggings With Quilted Puffer Jacket

In this outfit, black leggings are styled with a blue quilted puffer jacket and a white beanie. The leggings keep your base simple and fitted, and the jacket brings color and warmth.

You can add winter boots or sneakers depending on the weather. This look is great for walks, outdoor plans, or traveling when you need to be warm and comfortable but still want to look cute.

Cozy Monochrome Winter Whites

This combo plays with light colors: pale or grey leggings, a cropped top, and a white puffer jacket. The result is a cozy, winter-white look that feels fresh and on-trend.

White sneakers, a beanie, and sunglasses tie everything together. It’s a great outfit for daytime outings, snowy walks, or any time you want a bright, clean winter look that still feels warm.

Black Flare Leggings With Cream Hoodie

This outfit pairs black flare leggings with an oversized cream hoodie. The flares give a little movement and shape, while the hoodie keeps you comfortable and warm.

White sneakers finish the outfit and keep it casual. It’s ideal for everyday wear—errands, coffee, casual get-togethers—when you want something simple that still looks thoughtfully styled.

Faux Fur Coat With Navy Leggings

Here, navy leggings are worn under a bold faux fur coat. The leggings keep your legs warm and sleek, while the coat makes the whole outfit feel special and fun.

Combat boots and a small bag or clutch complete the look. It’s a great choice for evenings out, winter events, or any time you want to stay cozy while wearing a standout piece.

Polished Black Leggings With Tailored Coat

This outfit dresses up black leggings with a long grey wool coat and knee-high boots. The leggings act almost like thick tights, while the coat and boots make the whole look feel polished.

A structured bag in a warm brown tone adds a bit of contrast. This is a perfect winter city outfit—great for work, shopping, or meeting friends in a more refined setting.

Tailored Blazer With Dark Leggings Elegance

In this final look, dark leggings are paired with a navy blazer and a white shirt. The blazer sharpens the outfit, making the leggings feel more like slim trousers.

White sneakers and a small bag keep things relaxed but stylish. This is ideal for casual office days, meetings, or plans where you want to be comfortable but still look put-together and modern.