13 Winter Skirt Outfits That Are Warm and Fashion-Forward

Winter doesn’t have to mean saying goodbye to your favorite skirts. With the right layering, accessories, and fabrics, you can stay stylish and warm throughout the cold months. From cozy knits and knee-high boots to chic jackets and scarves, these winter skirt outfits will inspire you to rock your skirts all season long.

In this post, we’ve rounded up 13 trendy winter skirt outfits that will keep you feeling fabulous no matter the temperature. Whether you’re dressing for a casual day out, the office, or a night on the town, there’s something here for every occasion. So, let’s dive into these fashionable winter looks!

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1. Casual Cool: Denim Mini Skirt and Chunky Knits

Casual Cool Denim Mini Skirt and Chunky Knits

Create a laid-back winter look by pairing a blue denim mini skirt with a cozy ribbed sweater in neutral tones like cream or gray. Layer on a chunky knit scarf for extra warmth. Thick tights or knee-high socks will keep your legs toasty, while brown ankle boots finish the look perfectly. This outfit is great for a weekend coffee run or casual meet-ups with friends.

2. Sleek and Chic: Turtleneck and Maxi Skirt

Sleek and Chic Turtleneck and Maxi Skirt

For a more polished winter look, pair a fitted turtleneck with a dark, flowy maxi skirt. The long lines of the skirt and the turtleneck create a sophisticated silhouette. Knee-high boots add a touch of drama while keeping your legs warm. This outfit works perfectly for a dinner date or a professional setting.

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3. Romantic Flair: Puff Sleeves and Midi Skirt

Romantic Flair Puff Sleeves and Midi Skirt

For a feminine touch, combine a black puff-sleeve top with a rich burgundy midi skirt. Black knee-high boots and a vintage-inspired newsboy cap complete the look. This romantic yet edgy combination is ideal for a date night or a girls’ night out, bringing both warmth and style.

4. Classic with an Edge: Leather Mini and Camel Coat

Classic with an Edge Leather Mini and Camel Coat

For an outfit that balances classic and edgy, pair a white turtleneck with a black leather mini skirt, and layer a timeless camel coat over the top. Black tights and combat boots add a rebellious edge, while the camel coat keeps the ensemble polished. This outfit is perfect for those who love combining sophistication with a bit of rock ‘n’ roll.

5. Cozy Chic: Striped Sweater and Ribbed Maxi

Cozy Chic Striped Sweater and Ribbed Maxi

When comfort is key, go for a striped sweater paired with a ribbed maxi skirt in a coordinating color. Knee-high boots complete the look and provide warmth. This stylish and cozy outfit is ideal for casual weekends when you want to stay comfy yet chic.

6. Boho Winter: Turtleneck and Floral Maxi

Boho Winter Turtleneck and Floral Maxi

For a bohemian twist on winter style, pair a black turtleneck with a floral print maxi skirt. The floral pattern adds a pop of color to the neutral sweater, while knee-high boots ensure you stay warm. This look is perfect for brunches, casual workdays, or cozy gatherings with friends.

7. Bold and Bright: Oversized Coat and Sweater Dress

Bold and Bright Oversized Coat and Sweater Dress

When winter feels a little too gray, brighten things up with an oversized coat in a bold color, paired with a matching vibrant sweater dress. Add black over-the-knee boots for warmth and a touch of retro glamour. This outfit will make you feel energized and stylish, even on the darkest winter days.

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8. Preppy Cool: Sweatshirt and Plaid Mini

Preppy Cool Sweatshirt and Plaid Mini

Combine a casual black sweatshirt with a plaid mini skirt for a preppy yet edgy winter look. Black tights and lace-up boots keep you warm, while adding some tough-chic vibes. This outfit is perfect for a relaxed day out or a laid-back office environment.

9. Layered Textures: Ribbed Sweater and Plaid Mini

Layered Textures Ribbed Sweater and Plaid Mini

For a fun winter combination, layer a light-colored ribbed sweater over a dark plaid mini pencil skirt. Black knee-high socks paired with combat boots complete the look, adding a mix of textures and layers. This is the perfect outfit for shopping or meeting friends for coffee.

10. Sleek Monochrome: Crop Sweater and Maxi Skirt

Sleek Monochrome Crop Sweater and Maxi Skirt

Opt for an all-black ensemble for a sleek and modern winter look. Pair a black turtleneck crop sweater with a black maxi skirt featuring a side slit for a hint of drama. Layer black tights for warmth and finish the look with white chunky lace-up boots. The contrast of textures and proportions makes this outfit perfect for a night out.

11. Sweet and Feminine: Lace Collar and Midi Skirt

Sweet and Feminine Lace Collar and Midi Skirt

For a soft and delicate winter look, pair a white turtleneck sweater with a lace collar detail and a gray ribbed midi skirt. Black sheer tights and ankle boots provide warmth while maintaining a feminine vibe. This outfit is perfect for days when you want to feel pretty and put-together, even in the coldest weather.

12. Office Chic: Blazer and Geometric Skirt

Office Chic Blazer and Geometric Skirt

For a professional yet stylish winter outfit, layer a black turtleneck with a fitted black blazer, and add personality with a geometric print skirt. Black tights and pointed-toe shoes keep the look polished, while a structured handbag adds the finishing touch. This ensemble is perfect for a workday where you want to show your personality without compromising on professionalism.

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13. Boho Layers: Leather Jacket and Tiered Maxi

Boho Layers Leather Jacket and Tiered Maxi

For a boho-inspired winter outfit with a touch of edge, combine a striped top with a dark leather jacket and a tiered maxi skirt. Ankle boots keep the look winter-appropriate, while a wide-brim hat adds an extra boho touch. This ensemble is perfect for a night out or concert where you want to stand out while staying warm.

Conclusion

Winter skirts are more than just a spring or summer staple. With the right layers and accessories, you can style your skirts year-round without sacrificing warmth or style. From cozy knit sweaters and knee-high boots to bold coats and edgy leather skirts, there are countless ways to wear skirts throughout the cold months. Whether you’re dressing for the office, a dinner date, or a casual outing, these 13 winter skirt outfits will keep you warm, stylish, and confident.

Creative Fashionable Laound

Emily Parker

The founder of Chic Season Style, has always had an eye for fashion. With a deep love for how clothes can transform the way you feel, Emily Parker started Chic Season Style as a passion project with a simple goal: to create a space where women can feel inspired to dress boldly and authentically.

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