30+ Stylish Winter Outfits with Skirts: Stay Feminine and Warm

Are you feeling stuck in a winter wardrobe rut, thinking skirts are only for warmer days? Let’s banish that myth together and embrace the chilly months with style! On my blog, I’m sharing fabulous winter outfits featuring skirts that keep you both cozy and chic. Dive into my latest article to discover how you can transform your cold-weather looks with the right layering techniques and clever accessories—trust me, you’ll wonder why you didn’t try this sooner!

Casual Winter Outfits with Skirts: Chunky Turtleneck and Camel Midi Skirt Combo

Casual winter outfit with a chunky beige turtleneck, pleated camel midi skirt, and brown ankle boots.

This cozy winter ensemble features a chunky beige turtleneck sweater paired with a pleated camel-colored midi skirt, perfectly complemented by black tights and brown leather ankle boots. The combination is both stylish and comfortable, ideal for chilly days. Holding a steaming coffee cup, this look blends practical warmth with chic elegance, making it a great choice for embracing the season’s chill while staying fashionable.

Korean Winter Outfits Featuring Skirts and Cozy Knitwear

Korean winter outfit with cream sweater, pastel plaid mini skirt, and beige platform boots.

A young Korean woman in her twenties showcases a chic winter ensemble, combining a soft cream oversized sweater tucked into a pastel plaid A-line mini skirt. The addition of black tights and beige platform boots adds a stylish flair to her look. She stands by a city café, holding a scarf, perfectly blending comfort and fashion in the cold winter air. Her outfit effortlessly captures the essence of cozy urban style for the season.

Gray Wool Midi Skirt in Winter Outfits with Burgundy Turtleneck and Brown Boots

Winter outfit with a gray wool midi skirt, burgundy turtleneck, and brown knee-high boots.

This chic ensemble showcases a middle-aged woman in her thirties, effortlessly combining classic and contemporary styles. She dons a tailored wool gray midi skirt, perfectly paired with a fitted burgundy turtleneck. A long camel coat adds an elegant layer, while brown knee-high leather boots complete the look with a touch of timeless flair. Her black leather handbag complements the outfit, embodying a harmonious blend of practicality and style. Ideal for winter fashion enthusiasts seeking inspiration for a polished yet cozy look.

Stylish Winter Outfits Featuring Red Skirts and Ankle Boots

Winter outfit with a deep red pencil skirt, black sweater, and black suede ankle boots.

This winter ensemble perfectly balances elegance and comfort with a deep red pencil skirt and a black cashmere sweater. The addition of sheer black tights and black suede ankle boots creates a seamless look, complemented by a matching black scarf. Her bold red lip adds a pop of color, highlighting her confident style. This outfit is ideal for navigating the season with grace and poise, offering a chic take on winter fashion.

Navy Knit Sweater and Short Plaid Skirt Winter Outfit

Winter outfit with a navy knit sweater, short plaid skirt, and black combat boots.

A young woman in her twenties sports a stylish winter outfit that combines a navy blue knit sweater with a short plaid skirt in dark green and navy tones. Her look is completed with black tights and lace-up combat boots, adding a touch of rugged charm. A gray scarf draped loosely around her neck introduces an element of cozy elegance, making this ensemble both practical and chic for the chilly weather.

Vintage Winter Aesthetic: Oversized Sweater with Olive Skirt and Lace-Up Boots

Vintage winter outfit with a long olive skirt, cream oversized sweater, and brown lace-up boots.

This winter outfit channels a vintage-inspired vibe with its thoughtful blend of textures and tones. A long olive green wool skirt pairs beautifully with an oversized cream cable-knit sweater, creating a cozy yet elegant silhouette. Brown lace-up boots add a touch of rugged charm, while a dark brown felt hat ties the ensemble together with classic flair. Ideal for those who appreciate a timeless, winter-ready look that feels both nostalgic and fresh.

White Skirt Winter Outfit with Pale Blue Sweater and Fur-Lined Boots

Winter outfit with a white pleated skirt, pale blue sweater, and white fur-lined boots.

This outfit beautifully combines a white pleated midi skirt with a pale blue turtleneck sweater, creating a fresh and cozy look. Gray wool tights add an extra layer of comfort and warmth, perfectly paired with stylish white fur-lined boots. The fluffy white muff is a chic accessory, adding elegance to the ensemble. This look is ideal for those who appreciate a blend of style and comfort during the colder months.

Metallic Skirt and Lavender Puffer in Y2K Winter Outfit

Y2K winter outfit with a metallic silver mini skirt, cropped lavender puffer jacket, and platform sneakers.

Channeling early 2000s vibes, this winter ensemble features a metallic silver mini skirt paired with a cropped puffer jacket in a dreamy lavender hue. Black tights and platform sneakers add a modern twist, while a fluffy lavender bucket hat and mini shoulder bag complete the look with playful flair. This outfit seamlessly blends nostalgic elements with contemporary style for a chic and confident appearance.

Stylish Winter Outfits with Long Skirts and Cozy Layers

Winter outfit with a navy maxi skirt, black turtleneck, and wool plaid shawl.

This cozy winter outfit features a flowing navy blue maxi skirt paired with a classic black turtleneck sweater, creating a harmonious blend of style and comfort. The ensemble is accented by a wool plaid shawl in warm brown tones, adding a layer of texture and richness. Brown ankle boots complete the look, offering both practicality and flair. Ideal for embracing the chill with elegance, this outfit is a perfect choice for staying fashionable in cold weather.

Baddie Winter Outfit Featuring a Black Leather Skirt

Winter baddie outfit with a black leather mini skirt, white hoodie, and thigh-high black boots.

A young woman in her twenties rocks a sleek black leather mini skirt paired with an oversized white hoodie, creating a striking contrast that blends casual and edgy styles. Her fishnet tights and thigh-high black boots add a bold flair, while gold hoop earrings and sunglasses bring a touch of glam. This ensemble seamlessly balances comfort and fashion-forward attitude, making it perfect for those who love to mix different elements in their wardrobe.

Curvy Winter Outfits Featuring a Burgundy Wrap Skirt

Winter outfit with a burgundy wrap skirt, cream sweater, and heeled black ankle boots.

This chic winter ensemble features a curvy woman in her thirties, confidently styled in a burgundy wrap midi skirt paired with a cozy cream knit sweater. Black tights and heeled ankle boots add a sleek touch, while a plaid scarf provides an extra layer of warmth. Her radiant smile and confident stance perfectly capture the essence of effortless style and comfort for cold-weather outings.

Chic Winter Outfits with Grey Skirts and Houndstooth Blazer

Winter outfit with a charcoal gray pleated skirt, black turtleneck, and houndstooth blazer.

This cozy winter ensemble features a young woman in her twenties, effortlessly blending classic and contemporary styles. She dons a charcoal gray pleated skirt and a black turtleneck, both timeless pieces, paired with an oversized houndstooth blazer for a touch of vintage flair. Black tights and loafers complete the outfit, offering both warmth and comfort. Seated on snow-dusted stone steps, she enjoys a cup of tea, embodying a chic yet relaxed aesthetic perfect for the colder months.

Dark Denim Jeans Skirts Winter Outfit with Cream Sweater and Tan Boots

Winter outfit with a dark denim skirt, cream sweater, and tan suede knee-high boots.

This cozy winter outfit features a dark denim midi skirt paired with a cream chunky knit sweater, creating a blend of comfort and style. The knee-high tan suede boots complement the ensemble, while the brown shearling-lined jacket adds an extra layer of snugness. Topped off with a wool beanie and mittens, this look is perfect for a stroll on a chilly day, offering both warmth and elegance.

Stylish Winter Outfits with Knee-Length Skirts and Red Accents

Winter outfit with a black knee-length skirt, red turtleneck, and black heeled ankle boots.

This winter ensemble combines a tailored black knee-length skirt with a fitted red turtleneck, layered gracefully under a belted gray coat. Gray tights add an element of comfort and warmth, while black heeled ankle boots provide a touch of elegance. Completing the look is a chic leather handbag, perfect for any occasion. This outfit is ideal for embracing the chilly season with style and sophistication.

Chic Winter Outfits with Long White Skirts and Cozy Layers

Winter outfit with a long white pleated skirt, pink sweater, and beige wool coat.

This stylish winter ensemble features a long white pleated skirt paired with a soft pink cable-knit sweater, complemented by tan ankle boots. A beige wool coat provides an elegant layer, while a matching beige clutch adds a cohesive touch. This outfit effortlessly combines comfort and chic for a sophisticated winter look.

Navy Skirt Winter Outfit with Gray Sweater and Ankle Boots

Winter outfit with a navy pencil skirt, light gray sweater, and black ankle boots.

This winter ensemble features a navy blue pencil skirt paired with a light gray turtleneck sweater, creating a sleek and stylish silhouette. Black tights and black leather ankle boots add a touch of elegance, while the long navy coat offers warmth and structure. A silver scarf completes the look, adding a hint of metallic flair. Perfect for navigating the city in style during the colder months.

Blush Pink Skirt in Winter Outfits with White Sweater and Ankle Boots

Winter outfit with a blush pink skirt, white sweater, and white ankle boots.

This stylish winter ensemble features a soft blush pink A-line skirt paired with a classic white turtleneck sweater, cream tights, and chic white ankle boots. The combination offers a harmonious blend of pastel tones, creating a delicate and cozy aesthetic. Perfect for enjoying a warm drink on a snowy day, this outfit beautifully balances comfort and elegance, making it an ideal choice for a serene winter outing.

Winter Ensemble Featuring Red Skirt and Black Accents

Winter outfit with a long red pleated skirt, black sweater, and heeled black ankle boots.

This chic winter ensemble features a long red pleated skirt paired with a black cropped sweater, creating a striking contrast. The outfit is completed with black tights and heeled black ankle boots, offering both style and warmth. Perfect for a snowy outdoor market, this look captures the essence of winter fashion with its elegant yet cozy vibe, set beautifully under twinkling string lights.

Plaid Mini Skirt and Green Sweater Winter Outfit with Boots

Winter outfit with a plaid mini skirt, green sweater, and tall brown leather boots.

This winter ensemble features a plaid mini skirt in earthy tones, paired with a forest green knit sweater and tall brown leather boots. The combination of textures and colors creates a harmonious look, perfect for chilly weather. Draped over her arm, a gray wool coat adds an additional layer of style and practicality, making this outfit both fashionable and functional for snowy days.

Black Midi Skirt in Winter Outfits with Cream Sweater and Camel Trench Coat

Winter outfit with a black midi skirt, cream sweater, and camel trench coat.

This winter ensemble features a chic black A-line midi skirt paired with a cozy cream sweater, creating a stylish foundation for cold-weather dressing. The camel trench coat adds a timeless layer of sophistication, while black heeled ankle boots provide a sleek finish. This outfit effortlessly balances comfort and elegance, making it perfect for strolling through festive urban streets during the holiday season.

Grey Skirts Winter Outfit with Navy Sweater and Black Loafers

Winter outfit with a gray wool mini skirt, navy sweater, and black loafers.

This stylish winter ensemble combines a light gray wool mini skirt with a cozy navy knit sweater, perfect for chilly days. Navy tights provide a seamless look, complemented by classic black loafers that add a touch of timeless elegance. The navy scarf draped around the neck ties the outfit together, offering both warmth and style. Sitting on a snowy bench, this look is ideal for anyone seeking a chic yet comfortable winter outfit.

Vintage Skirts: Aesthetic Winter Outfits for Women

Vintage winter outfit with a green plaid skirt, white blouse, and cropped cream cardigan.

This vintage-inspired winter ensemble features a dark green plaid midi skirt paired with a white high-neck blouse, creating a timeless and elegant silhouette. A cropped cream cardigan adds warmth and texture, while the dark brown wool beret introduces a classic touch. Lace-up boots complete the look, blending practicality with style for a charming, retro aesthetic. Perfect for those who appreciate a nostalgic nod to fashion in the colder months.

Girly Cute Winter Outfit Featuring a Skirt and Ankle Boots

Cute winter outfit with a baby pink skirt, white sweater, and white ankle boots.

This stylish winter ensemble features a flared baby pink skirt paired with a white knit sweater adorned with charming puffed sleeves. Cream tights and white ankle boots create a cohesive, elegant look, while the fluffy white earmuffs add a playful touch. Perfect for those chilly days when you want to combine warmth with a hint of whimsy.

Stylish Winter Outfits Featuring Long Jean Skirts

Winter outfit with a long denim skirt, black turtleneck, and camel belted coat.

This stylish winter ensemble features a full-length dark denim skirt paired with a sleek black fitted turtleneck, creating a timeless and chic foundation. The camel belted coat adds a layer of warmth and elegance, perfectly complemented by tan leather ankle boots for a touch of rustic charm. This outfit effortlessly blends classic and contemporary elements, making it an ideal choice for embracing the cozy vibes of the season.

Korean Winter Short Skirts Outfit with Knee-High Boots

Korean winter outfit with a short beige pleated skirt, cream sweater, and brown knee-high boots.

This winter ensemble features a young Korean woman dressed in a chic combination of a short beige pleated skirt and a cozy cream oversized sweater. Paired with black tights and knee-high brown boots, the outfit strikes a balance between comfort and style. The addition of a knit beret adds a playful yet sophisticated touch, perfectly complementing the overall look. The attire is an ideal choice for those looking to stay warm and stylish during the colder months.

Plaid Midi Skirt and Wool Coat: Winter Outfits with Skirts and Sweater

Winter outfit with a plaid midi skirt, gray sweater, and dark green wool coat.

This winter ensemble perfectly blends comfort and style, featuring a plaid A-line midi skirt paired with a light gray sweater for a cozy, chic vibe. The long dark green wool coat adds a layer of warmth and elegance, while black leather ankle boots provide a sleek finish. Ideal for strolling through snowy streets, this outfit embodies a harmonious mix of classic and contemporary fashion.

Stylish Winter Outfits Featuring Brown Skirts

Winter outfit with a brown corduroy skirt, beige turtleneck, and brown ankle boots.

This winter ensemble features a harmonious blend of cozy and chic elements. A brown corduroy midi skirt pairs seamlessly with a beige turtleneck sweater, creating a warm and inviting look. Brown tights and heeled ankle boots complement the outfit, adding a touch of elegance and cohesion. The tan leather handbag is both practical and stylish, serving as the perfect accessory for navigating snowy cobblestone streets with flair.

Nice Winter Outfits Featuring Classy Skirts

Classy winter outfit with a black silk skirt, white blouse, and gray blazer.

This chic ensemble features a black silk midi skirt paired with a fitted white blouse and a tailored gray blazer. The outfit is completed with black heeled boots and a sleek black clutch. Perfect for a sophisticated look, this combination blends classic elegance with modern flair, ideal for any professional setting or stylish occasion.

Elegant Winter Outfits Featuring Long Skirts and Cozy Layers

Winter outfit with a long beige pleated skirt, cream sweater, and brown lace-up boots.

This stylish winter ensemble features a long beige pleated skirt paired with a soft cream sweater, complemented by black tights and brown lace-up boots. The combination showcases a harmonious blend of neutral tones, offering both elegance and comfort. Perfect for embracing the chilly season with a touch of sophistication, this outfit effortlessly balances warmth and fashion-forward flair.

Chic Winter Look Featuring Knee-Length Skirt and Sweater Combo

Winter outfit with a black knee-length skirt, maroon sweater, and black ankle boots.

This winter ensemble showcases a black knee-length pencil skirt paired with a maroon sweater, creating a sophisticated contrast. The addition of black tights and leather ankle boots adds a sleek touch, while the maroon scarf provides an element of warmth and style. Perfect for navigating the snowy city streets, this outfit blends functionality with chic elegance, making it an ideal choice for cold-weather fashion.

Green Sweater and White Sneakers in Winter Outfits with Tennis Skirts

Winter outfit with a white tennis skirt, green sweater, and white sneakers.

A chic winter ensemble combines a forest green oversized sweater with a crisp white tennis skirt for a sporty yet cozy look. Paired with knee-high white socks and classic white sneakers, this outfit effortlessly blends comfort and style. The snowy tennis court setting adds a touch of seasonal charm, while the light frost on the racket hints at a playful and dynamic spirit. This look captures the essence of winter fashion with its clean lines and harmonious color palette.

Chic Winter Look Featuring Black Skirts Outfits

Winter outfit with a black pleated skirt, beige turtleneck, and black heeled ankle boots.

This chic winter ensemble features a black pleated midi skirt paired with a light beige turtleneck and black tights, creating a harmonious blend of classic and modern styles. The look is completed with black heeled ankle boots and a long beige coat, adding an elegant touch to the outfit. Perfect for those cold days, this outfit balances warmth with sophistication, ideal for embracing the season in style.

Plaid Skirt and Sweater Vest in Preppy Winter Outfits

Preppy winter outfit with a plaid skirt, white shirt, and gray sweater vest.

This stylish ensemble showcases a plaid pleated skirt in navy and burgundy hues, paired with a crisp white button-up shirt and a cozy gray sweater vest. Knee-high brown boots add a classic touch, while the brown satchel bag completes the look with practicality and flair. Perfect for navigating a snow-covered university campus, this outfit blends timeless elements with contemporary charm.

Stylish Winter Outfits Featuring Cargo Skirts

Winter outfit with an olive green cargo skirt, black puffer jacket, and black combat boots.

This chic winter ensemble features an olive green cargo skirt paired with a black cropped puffer jacket for a modern, utilitarian vibe. The look is grounded by black combat boots and thermal leggings, providing both warmth and style. A black beanie, casually held in one hand, adds a practical yet fashionable touch to this cold-weather outfit, perfect for navigating snowy paths with confidence.