20 Chic Leggings Outfits for Winter That’ll Keep You Warm and Stylish All Season Long

Winter doesn’t have to mean choosing between being cold or wearing bulky clothes. Leggings are a versatile solution, letting you stay warm without giving up style. Paired with the right tops and layers, they can create chic outfits for coffee runs, casual dinners, or winter outings. Here are 20 combinations that prove leggings can be stylish and cozy all season.

Cozy Cropped Sweatshirt and Black Leggings

A cropped sweatshirt with fitted black leggings offers warmth and a flattering shape. High-waisted leggings balance the proportions, and white sneakers complete a casual, sporty look suitable for errands or a casual day out.

Cozy Cropped Sweatshirt and Black Leggings

Black Leggings with Puffed Jacket and Scarf

Pairing black leggings with a quilted puffer jacket and a large scarf creates a warm yet polished winter look. Accessories like a structured crossbody bag add practicality while keeping the outfit elegant and comfortable.

Black Leggings with Puffed Jacket and Scarf

Monochrome Casual with Sporty Sneakers

Black leggings with an oversized cream sweatshirt and white platform sneakers form a simple, cozy outfit. The monochrome palette keeps it stylish while layering provides warmth for winter outings.

Monochrome Casual with Sporty Sneakers

Cozy Sweatshirt with Burgundy Leggings

A neutral oversized sweatshirt paired with jewel-toned burgundy leggings creates a chic, balanced look. White sneakers ground the outfit, perfect for casual days, brunch, or errands.

Cozy Sweatshirt with Burgundy Leggings

Cozy Cream Sweatshirt and Black Leggings

This combination uses a cream sweatshirt with black leggings for an effortlessly chic winter outfit. Monochrome tones elongate the legs and keep the look simple and versatile for casual activities.

Cozy Cream Sweatshirt and Black Leggings

Oversized Hoodie and Black Leggings

Black leggings and an oversized hoodie provide warmth and comfort with a casual-cool aesthetic. White sneakers complete the look, making it easy to wear for errands or relaxing days.

Oversized Hoodie and Black Leggings

Striped Top with Flare Leggings

A striped shirt with navy flare leggings creates a polished yet comfortable outfit. Flared leggings elongate the silhouette, while casual sneakers and a crossbody bag complete this versatile winter look.

Striped Top with Flare Leggings

Houndstooth Jacket with Black Leggings

Black leggings paired with a houndstooth jacket offer a refined winter outfit. The patterned jacket adds sophistication, and fitted leggings maintain warmth and a sleek silhouette.

Houndstooth Jacket with Black Leggings

Striped Sweater with Classic Black Leggings

Oversized striped turtleneck sweaters with black leggings balance cozy volume with sleek lines. Pointed flats finish the look for casual or semi-formal winter activities.

Striped Sweater with Classic Black Leggings

Black Leggings with Cream Cardigan Layers

Black leggings under a cream cardigan create a warm, layered winter outfit. The cardigan adds dimension while maintaining a polished, versatile look for day-to-night wear.

Black Leggings with Cream Cardigan Layers

Burgundy Cardigan with Black Leggings

A burgundy cable-knit cardigan paired with black leggings offers a flattering, cozy winter outfit. Knee-high boots and a structured bag complete the chic ensemble.

Burgundy Cardigan with Black Leggings

Camel Vest with Tan Leggings

Neutral-toned leggings with a camel vest provide a comfortable, modern winter look. White sneakers and subtle layering keep it stylish and versatile for casual occasions.

Camel Vest with Tan Leggings

Cream Blazer with Chocolate Flare Leggings

A cream blazer with chocolate brown flare leggings elevates winter leggings into a chic, sophisticated outfit. Flared cuts add visual interest while white sneakers provide a modern edge.

Cream Blazer with Chocolate Flare Leggings

Black Flare Leggings with Puffer Jacket

High-waisted black flare leggings paired with a black puffer jacket combine warmth with contemporary style. White sneakers add contrast, making this outfit versatile for day-to-night wear.

Black Flare Leggings with Puffer Jacket

Black Leggings With Quilted Puffer Jacket

Black leggings with a blue quilted puffer jacket balance comfort and chic style. Accessories like a white beanie complete the look for cold-weather outings.

Black Leggings With Quilted Puffer Jacket

Cozy Monochrome Winter Whites

A white ensemble with light gray leggings and a cropped pink top under a white puffer jacket creates a winter-ready, fashionable monochrome outfit. Sneakers and accessories complete the style.

Cozy Monochrome Winter Whites

Black Flare Leggings with Cream Hoodie

Black flare leggings with an oversized cream hoodie provide a comfortable yet stylish winter look. White sneakers and a simple color palette keep the outfit modern and versatile.

Black Flare Leggings with Cream Hoodie

Faux Fur Coat with Navy Leggings

Navy leggings with a bold faux fur coat create a winter outfit that is both warm and fashion-forward. Accessories like a beret and boots complete the elevated look.

Faux Fur Coat with Navy Leggings

Polished Black Leggings with Tailored Coat

Black leggings under a gray wool coat provide a refined, polished winter outfit. Knee-high boots and a leather tote finish a chic, city-ready look.

Polished Black Leggings with Tailored Coat

Tailored Blazer with Dark Leggings Elegance

Dark leggings paired with a navy blazer and crisp shirt create a sophisticated, office-appropriate winter outfit. Sneakers and a mini bag add comfort and a casual-chic touch.

Tailored Blazer with Dark Leggings Elegance

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