30+ Cozy and Cute Winter Outfits with Leggings for Every Occasion

Black leggings with an oversized knit sweater and a puffer jacket, styled casually for winter.

Struggling to stay stylish and warm during those chilly winter months? Trust me, I’ve been there, wondering how to keep cozy without sacrificing fashion. Enter leggings—a versatile staple that can transform your winter wardrobe from drab to fab. Dive into my latest article where I share the ultimate guide to chic winter outfits with leggings, proving that comfort and style can indeed go hand in hand.

Winter Outfits Featuring Brown Leggings and Camel Coat Combo

Brown leggings styled with a beige sweater, camel coat, and boots, perfect for winter.

This ensemble perfectly captures a cozy winter vibe. Featuring brown fleece-lined leggings paired with an oversized beige knit sweater, it’s both comfortable and stylish. The camel-colored wool coat adds a layer of chic elegance, while ankle boots provide practicality for colder days. A chunky cream scarf ties the whole look together, making it ideal for staying warm and fashionable during the chilly season.

Casual Winter Outfits with Leggings and Layers

Casual winter outfit featuring black leggings, a gray hoodie, and a black vest for cold weather.

A modern ensemble featuring black thermal leggings paired with a long gray hoodie and a puffy black vest creates a chic, layered look. White sneakers add a crisp touch, while a black beanie tops off the outfit, offering both style and comfort. Perfect for navigating the urban landscape with ease and flair.

Dressy Winter Outfit with Leggings and Tailored Coat

Dressy winter outfit with black faux-leather leggings, a red blouse, and a tailored black coat.

This ensemble showcases a chic blend of textures and colors, featuring black faux-leather leggings that offer a sleek foundation. Paired with a red satin blouse, the outfit brings a touch of bold elegance, while the tailored black coat adds a layer of refinement. Heeled ankle boots complete the look, providing a sophisticated edge. The clutch bag serves as a practical yet stylish accessory, perfect for an evening out in the city.

Winter Outfits Featuring Green Leggings and Tan Knee-High Boots

Winter outfit with green leggings, a cream turtleneck, and tan knee-high boots.

This chic winter ensemble features forest green leggings paired with a cozy cream turtleneck sweater, perfectly complemented by a brown shearling jacket. Tan knee-high boots add a stylish touch, making this outfit ideal for a snowy day. It’s a harmonious blend of comfort and fashion, perfect for embracing the cold season with style and grace.

Cozy Winter Look with Gray Leggings and Black High Top Converse

Winter outfit with gray leggings, a black hoodie, and Converse sneakers.

This urban winter outfit features a casual yet stylish combination of black high-top Converse sneakers and gray leggings, perfect for a laid-back city stroll. The oversized black hoodie adds a cozy layer, while a plaid scarf provides both warmth and a touch of pattern to the ensemble. Ideal for navigating chilly city streets, this look balances comfort and casual style with ease.

Korean Winter Leggings Outfit with Camel Sweater and Beige Trench Coat

Korean winter outfit with black leggings, a camel sweater, and a beige trench coat.

This stylish ensemble perfectly balances comfort and elegance with black leggings and an oversized camel sweater, topped with a long beige trench coat. The look is completed with black ankle boots and a small crossbody bag, ideal for navigating urban streets with flair. The combination of neutral tones and sleek footwear offers a chic yet practical outfit, ideal for colder days.

Winter Outfit Featuring Burgundy Leggings and Gray Coat

Winter outfit with burgundy leggings, a white sweater, and a gray coat.

This winter ensemble combines the coziness of a white knit sweater with the sleekness of burgundy leggings. A charcoal gray wool coat offers a classic touch, paired perfectly with black riding boots for a refined finish. Topping off the look, a matching gray knit hat adds both warmth and style, making this outfit a chic choice for chilly days.

Navy Leggings and Olive Vest Outfits for Women in Winter

Winter outfit with navy leggings, a white shirt, and an olive vest.

This winter ensemble combines practicality and style with navy leggings and a white long-sleeve thermal shirt, layered under a quilted olive-green vest for added warmth. The tan snow boots not only provide comfort but also add a complementary touch to the outfit, making it perfect for exploring snowy trails.

Stylish Winter Look: Cream Sweater and Green Puffer with Leggings Over 40

Winter outfit for women over 40 with black leggings, a cream sweater, and a green puffer coat.

This cozy winter ensemble features sleek black knee-high boots paired with classic black leggings, creating a streamlined silhouette. A cream tunic sweater adds a layer of warmth and softness, while the long dark green puffer coat provides both style and insulation against the cold. The outfit is finished with a knit scarf, offering an extra touch of coziness perfect for brisk days. This combination is ideal for staying chic and comfortable during the colder months.

Gray Leggings and Navy Sweater for Chic Winter Outfits with Boots

Winter outfit with gray leggings, a navy sweater, and brown knee-high boots.

This stylish winter ensemble features gray wool leggings paired with a navy cable-knit sweater, topped with a tan suede coat for a cozy yet fashionable look. Brown knee-high boots complement the outfit, along with a matching crossbody bag for practicality and flair. Perfect for navigating chilly urban landscapes, this outfit combines comfort and style seamlessly.

Cute Winter Outfits with Black Leggings and Cozy Layers

Cute winter outfit with black leggings, a pink sweater, and a white sherpa jacket.

This cozy winter ensemble features sleek black leggings paired with an oversized pink sweater, creating a perfect balance of comfort and style. The white sherpa jacket adds an extra layer of warmth, while white sneakers keep the look casual and fresh. Topping it all off, a pom-pom beanie brings a playful touch to this chic outfit, ideal for embracing the chilly season with flair.

Cozy Winter Look: Gray Leggings and Sherpa-Lined Jean Jacket Outfit

Winter outfit with gray leggings, a turtleneck, and a sherpa-lined denim jacket.

This stylish ensemble features dark gray leggings paired with a cozy cream turtleneck and a sherpa-lined denim jacket, offering both comfort and warmth. Black combat boots add a touch of rugged flair, while the plaid scarf introduces a classic pattern to the look. Perfect for embracing the winter chill with effortless style.

Midsize Winter Outfits: Black Leggings with Maroon Sweater and Tan Teddy Coat

Midsize winter outfit with black leggings, a maroon sweater, and a tan teddy coat.

A stylish ensemble perfect for a snowy day, featuring black leggings paired with an oversized maroon sweater and a cozy tan teddy coat. This look is completed with ankle boots and a knit scarf, blending comfort and fashion seamlessly for chilly weather. Ideal for sipping coffee on a frosty patio, the outfit combines practicality with a chic flair, offering warmth without sacrificing style.

Casual Winter Outfit Featuring Green Leggings for Rainy Days

Casual winter outfit for rainy days with green leggings, a cream sweater, and a black raincoat.

This chic outfit is perfect for a rainy day, combining style and practicality. The ensemble features olive-green waterproof leggings, adding a unique touch to the overall look. A cream cable-knit sweater offers warmth and texture, while a black rain jacket with a hood provides essential protection against the elements. Waterproof black boots complete the outfit, ensuring comfort and durability in wet conditions. This combination is both functional and fashionable, making it an ideal choice for navigating the city streets in style during rainy weather.

Burgundy Sweater and Gray Parka with Thermal Leggings for Winter Outfits

Winter outfit with thermal black leggings, a burgundy sweater, and a gray parka.

This stylish winter ensemble features sleek black thermal leggings paired with a cozy burgundy turtleneck sweater, perfectly complemented by a gray parka. The look is completed with fur-lined winter boots and gloves, creating a chic and practical outfit ideal for cold-weather adventures. Perfectly suited for both comfort and style, this outfit is a testament to effortless winter fashion.

Casual Winter Outfits Featuring Leggings and Uggs

Casual winter outfit with beige leggings, a brown hoodie, and chestnut Ugg boots.

This cozy winter ensemble combines beige leggings with an oversized brown hoodie and a white puffy vest, creating a relaxed yet stylish look. Chestnut Ugg boots complement the outfit, offering both warmth and comfort. Perfect for a stroll through snowy streets adorned with holiday lights, this outfit balances casual comfort with seasonal flair.

Black Leggings and Vest in a Cozy Winter Outfit

Winter outfit with black leggings, a gray shirt, and a quilted black vest.

This cozy winter outfit features a chic combination of black leggings and a light gray thermal shirt, layered with a stylish black quilted vest. Complemented by gray snow boots and a knit hat, the ensemble perfectly balances functionality and style for cold weather. This look showcases how to stay warm while maintaining a fashionable edge during the winter months.

New York Aesthetic Winter Outfit with Leggings and a Trench Coat

Winter New York-style outfit with black leggings, a gray sweater, and a camel trench coat.

This chic winter ensemble effortlessly combines comfort and style on the bustling streets of New York City. The outfit features black leggings paired with an oversized dark gray sweater, layered under a classic camel trench coat for a timeless appeal. Black ankle boots add a sleek touch, while a leather tote bag offers practicality and flair. This look is perfect for navigating the city in both warmth and fashion-forward elegance.

Preppy Winter Outfits Featuring Black Leggings and Navy Sweater

Preppy winter outfit with black leggings, a navy sweater, and a plaid scarf.

This winter ensemble combines classic pieces for a stylish look. A navy cable-knit sweater is layered over a crisp white button-down shirt, paired with black leggings for a sleek silhouette. The plaid scarf adds a touch of pattern and texture, while black loafers offer both comfort and style. A structured handbag completes the look, providing a polished finish to this chic outfit. Perfect for those chilly days when you want to stay cozy yet fashionable.

January Mom Leggings Outfit with Cozy Winter Layers

Winter mom outfit with navy leggings, a white sweater, and a beige puffer coat.

A stylish winter ensemble perfect for braving chilly days. The outfit features navy thermal leggings paired with a cozy white knit sweater, topped with a long beige puffer coat for extra insulation. Waterproof brown boots offer both practicality and style, while a diaper bag adds a functional yet fashionable touch. Ideal for keeping comfortable and chic in the cold.

Cozy Winter Outfits Featuring Red Leggings

Winter outfit with red leggings, a black sweater, and a gray coat.

This winter ensemble showcases a chic combination of red thermal leggings paired with a classic black turtleneck sweater, layered under a long gray coat for a stylish contrast. The look is completed with black snow boots, offering both practicality and flair. Perfect for those cold days when you want to stay cozy yet fashionable.

Teacher Winter Outfit: Black Leggings with Mustard Sweater and Navy Cardigan

Winter teacher outfit with black leggings, a mustard sweater, and a navy cardigan.

This ensemble combines the ease of black leggings with a mustard yellow tunic sweater, layered under a long navy cardigan. The brown ankle boots add an earthy touch, creating a cozy and stylish outfit perfect for a chilly day. The combination of colors and textures in this outfit makes it both comfortable and chic, ideal for those seeking warmth without compromising on style.

Casual Winter Look with Gray Leggings and Black Vans Sneakers

Winter outfit with gray leggings, a hoodie, and black Vans sneakers.

The ensemble features a stylish combination of gray leggings and a black hoodie, paired with a crisp white puffer jacket. The outfit is completed with black Vans sneakers, adding a casual yet chic touch. A black backpack is slung over the shoulder, offering both practicality and style as she walks along a frosty urban sidewalk. This look effortlessly blends comfort with modern streetwear aesthetics.

Cozy Winter Outfits with Leggings and Uggs

Winter outfit with black leggings, a cream sweater, and tan Ugg boots.

This cozy ensemble effortlessly combines comfort and style, featuring black leggings paired with a cream knit sweater and a light tan puffy vest. The chestnut Ugg boots add a classic touch, perfect for keeping warm during chilly days. This outfit offers a harmonious blend of textures and colors, ideal for casual outings or relaxed winter gatherings.

Girly Winter Outfits Featuring Pink Leggings and Cozy Sweater

Girly winter outfit with pink leggings, a white sweater, and a matching scarf.

This cozy winter ensemble features blush pink leggings paired with a white oversized sweater and a matching blush pink scarf. The look is completed with beige ankle boots, creating a harmonious blend of soft tones perfect for the season. Ideal for embracing chilly days in style, this outfit offers both comfort and elegance.

Navy Leggings and Dark Green Parka: Cozy Winter Outfit Combination

Winter outfit with navy leggings, a beige sweater, and a dark green parka.

This cozy winter ensemble is perfect for cold-weather outings. Featuring navy leggings paired with a beige knit sweater, the outfit is topped with a long dark green parka jacket for added warmth. Black snow boots ensure comfort and practicality, while the fur-trimmed hood adds a touch of snug elegance. Ideal for blending comfort with style during frosty days.

Stylish Winter Mom Outfit Featuring Gray Leggings

Winter mom outfit with gray leggings, a maroon sweater, and a beige jacket.

This cozy winter ensemble features a stylish blend of comfort and functionality. The maroon cowl-neck sweater pairs beautifully with gray leggings, offering a relaxed yet chic vibe. A beige quilted jacket adds an extra layer of warmth, perfect for chilly days. Waterproof black boots ensure practicality without compromising on style, while a knit hat tops off the look with a touch of coziness. Ideal for enjoying the season’s brisk outdoor adventures with flair and comfort.

Navy Leggings and Sweater Vest in Preppy Winter Outfit

Preppy winter outfit with navy leggings, a plaid blazer, and a sweater vest.

This stylish ensemble features navy leggings paired with a crisp white collared shirt, layered under a classic gray sweater vest. A plaid blazer adds a touch of timeless elegance, while brown loafers ground the look in sophistication. Perfect for those who appreciate a blend of classic and contemporary fashion, this outfit effortlessly balances comfort and style.

Cream Leggings and Uggs in a Cozy Winter Outfit

Winter outfit with cream leggings, a pink hoodie, and chestnut Ugg boots.

This cozy winter outfit features cream leggings paired with a light pink oversized hoodie, layered under a beige puffer coat for extra warmth. The ensemble is completed with chestnut Ugg boots, creating a harmonious blend of soft, neutral tones perfect for the colder months. The combination of textures and muted colors offers a chic yet comfortable look, ideal for embracing winter fashion with ease.

Black Leggings with Vans for a Cozy Winter Outfit

Winter outfit with black leggings, a red hoodie, and black Vans sneakers.

This stylish ensemble showcases a perfect blend of casual and chic elements, featuring black leggings paired with a red oversized hoodie for a relaxed vibe. The addition of a black bomber jacket introduces a sleek touch, while black Vans sneakers complete the look with classic flair. This outfit effortlessly combines comfort and style, making it ideal for navigating the urban landscape with confidence.

Stylish Winter Outfits Featuring Leggings and a Camel Coat

Winter outfit with black leggings, a gray sweater, and a camel coat.

This stylish ensemble features black leggings paired with a light gray sweater and a tailored camel coat. Black ankle boots add a touch of chic to the outfit, while a black crossbody bag provides practicality and flair. Perfect for navigating snowy city streets with elegance, this look balances comfort and sophistication effortlessly.

Burgundy Blouse and Black Velvet Leggings for Dressy Winter Outfits

Dressy winter outfit with black velvet leggings, a burgundy blouse, and a black coat.

This holiday party ensemble showcases a sophisticated blend of textures and colors. The outfit features black velvet leggings paired with a luxurious burgundy silk blouse, complemented by a long black wool coat. Heeled ankle boots add an elegant lift, while eye-catching earrings provide a touch of glamour. Perfect for celebrating the season in style.

Cozy Winter Flannel Outfit with Black Leggings

Winter outfit with black leggings, a red flannel shirt, and a quilted vest.

This winter ensemble effortlessly combines comfort and style with black leggings and a red-and-black flannel shirt layered under a black quilted vest. Brown ankle boots add a rustic touch, making it an ideal outfit for those crisp, snowy days. The look is both practical and fashionable, perfect for embracing the cold with confidence and flair.

Grunge Winter Outfits Featuring Leggings and Plaid Coat

Grunge winter outfit with ripped black leggings, a black sweater, and a plaid coat.

A chic winter ensemble features ripped black leggings paired with a cozy, oversized black sweater, layered under a striking red plaid coat. Black combat boots add a touch of rugged style, while a chain necklace offers a subtle edge. This outfit effortlessly combines comfort and fashion, perfect for those who want to stay warm without sacrificing style during the colder months.

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