20 Winter Skirt Outfits That Define Cozy Elegance
Winter fashion doesn’t mean saying goodbye to skirts — in fact, it’s the season to elevate them with cozy layers, warm textures, and creative styling. Whether it’s pairing chunky knits with pleated minis or adding structured coats for contrast, the right winter skirt outfit can strike the perfect balance between warmth and sophistication.
From timeless neutrals to chic layering, these looks bring out the softer side of winter dressing. Each outfit blends practicality with trend-driven appeal, showing how skirts can remain a wardrobe staple even on the coldest days. Let’s dive into twenty stunning winter skirt outfits that prove elegance and comfort can absolutely coexist.
1. Cable Knit Sweater with Layered Shirt & Plaid Mini Skirt
A cable knit sweater layered over a crisp shirt and paired with a plaid mini skirt is the definition of preppy winter charm. The combination of cozy textures and classic prints gives this look a refined yet youthful edge. Perfect for coffee dates or casual strolls through the city, it blends comfort and sophistication effortlessly. Add tights and ankle boots to stay warm while keeping that timeless winter aesthetic intact.
2. Chic Layered Look with Brown Blazer & Mini Skirt
This chic layered ensemble featuring a tailored brown blazer and mini skirt embodies understated city elegance. The structured silhouette of the blazer contrasts beautifully with the femininity of the skirt, creating a polished yet playful vibe. Ideal for brunches, museum visits, or even office-ready winter days, this look balances warmth with a sharp, stylish flair that feels effortlessly modern.
3. Cable Knit Sweater with Split Hem Jeans & Cozy Scarf
A cozy cable knit sweater paired with split-hem jeans and a soft scarf offers the perfect blend of casual comfort and refined texture. While not skirt-focused, the relaxed silhouette complements colder days when you crave coziness with style. The scarf adds a layer of warmth and softness, creating an ensemble ideal for relaxed weekends or winter travel days in the city.
4. Chunky Knit Sweater with Mini Skirt & Cozy Leg Warmers
A chunky knit sweater and mini skirt combo brings playful nostalgia to winter fashion, especially when paired with leg warmers. The look feels effortlessly retro yet perfectly current. It’s a cozy, layered outfit that works beautifully for casual outings, festive gatherings, or laid-back winter weekends. The leg warmers not only add warmth but also give the outfit an irresistibly cute, seasonal touch.
5. Turtleneck Mini Dress with Cropped Jacket & Knee-High Boots
A turtleneck mini dress layered under a cropped jacket and paired with knee-high boots delivers instant winter chic. The silhouette is sleek yet cozy, making it ideal for both day and night. Whether you’re out for dinner or exploring city streets, this outfit radiates confidence and sophistication. The mix of textures keeps it balanced — structured outerwear meets soft knits in true cold-weather harmony.
6. Chunky Knit Sweater Over Collared Shirt with Pleated Mini Skirt
A chunky knit sweater worn over a collared shirt and paired with a pleated mini skirt channels classic school-girl energy with a grown-up twist. The layered details add dimension and coziness, while the pleats introduce movement and charm. Perfect for chilly morning errands or weekend coffee catch-ups, this outfit embodies effortless winter preppy style.
7. Gray Ribbed Hoodie, Black Pleated Skirt & Deep-Brown Long Coat
This look defines modern winter layering with its balanced textures and tones. The gray ribbed hoodie gives casual comfort, the black pleated skirt adds movement, and the deep-brown coat ties everything together with urban sophistication. It’s perfect for transitional weather or days when you want warmth without sacrificing edge — the ultimate example of chic comfort.
8. Brown and White Striped Sweater with White Pleated Skirt
A brown and white striped sweater with a white pleated skirt feels crisp, fresh, and full of cozy charm. The color palette brightens winter’s gloom while keeping the outfit refined and easy to wear. Ideal for daytime outings or brunch dates, it’s a minimalist yet feminine combination that feels both warm and polished.
9. All-Black Pleated Skirt with Sheer Polka Dot Tights
An all-black pleated skirt paired with sheer polka dot tights delivers a bold yet sophisticated statement. The monochrome aesthetic gives it versatility — perfect for evenings out or stylish city strolls. The subtle pattern of the tights adds intrigue without overpowering the outfit, creating a look that’s both refined and flirty.
10. Black Long Coat with White Maxi Style Skirt and Gold-Buckled Belt
This ensemble exudes timeless elegance. The black long coat paired with a flowing white maxi skirt creates striking contrast, while the gold-buckled belt adds a refined focal point. It’s a statement-making outfit for winter events or formal gatherings, combining dramatic silhouettes with soft, graceful movement.
11. Off-Shoulder Cream Sweater with Brown Pleated Skirt and Beige Suede Boots
A soft off-shoulder cream sweater paired with a brown pleated skirt creates a dreamy, feminine look that feels effortlessly romantic. The beige suede boots enhance the cozy aesthetic, grounding the outfit while keeping it refined. Perfect for casual winter lunches or cozy evening plans, it’s a warm embrace of comfort and style.
12. Striped Brown and White Knit Cardigan with White Pleated Skirt
This look strikes the perfect harmony between coziness and sophistication. The striped cardigan adds warmth and visual interest, while the white pleated skirt keeps the outfit crisp and elegant. Perfect for transitional winter days, this combination feels polished yet easygoing — a true balance of modern femininity and comfort.
13. Grey Oversized Sweater with Pleated Grey Skirt and Black Knee-High Boots
Monochrome lovers will adore this sleek grey-on-grey outfit. The oversized sweater pairs beautifully with the pleated skirt for a cozy yet structured feel, while the black knee-high boots lend a touch of edge. This look works wonderfully for casual city days or cozy winter afternoons, embracing texture and tone in a subtly chic way.
14. Taupe Oversized Blazer with White Top and Black Slit Maxi Skirt
Refined and effortlessly modern, this outfit pairs a taupe oversized blazer with a white top and black slit maxi skirt for an elevated city look. The sleek lines of the skirt contrast with the relaxed fit of the blazer, creating a powerful yet feminine outfit. Perfect for a workday or evening dinner, it’s minimalism at its most sophisticated.
15. Off-Shoulder Cream Sweater with Brown Pleated Skirt and Tan Suede Boots
Romantic and timeless, this outfit pairs an off-shoulder sweater with a pleated skirt in rich winter tones. The tan suede boots complete the look with soft texture and warmth. Whether it’s a holiday outing or casual weekend plans, this ensemble radiates charm and seasonal elegance.
16. Black and White Varsity Sweater with Grey Fuzzy Skirt and Black Knee-High Boots
Sporty meets chic in this playful winter combo. The black and white varsity sweater adds a youthful twist, while the fuzzy grey skirt keeps it cozy and fashion-forward. Paired with knee-high boots, it’s a fun yet stylish outfit that’s perfect for everyday wear — a fresh take on winter street style.
17. Cream Ribbed Sweater with Black Leopard Print Skirt and Black Combat Boots
This outfit embraces contrast and confidence. The cream ribbed sweater softens the boldness of the leopard print skirt, while black combat boots add an edgy finish. It’s the ideal choice for fashion lovers who like mixing feminine details with street-style strength, making every winter day feel bold and empowering.
18. Grey Cropped Cardigan with White Tank and Pleated Grey Mini Skirt
A cropped cardigan layered over a white tank and styled with a pleated grey mini skirt gives off cozy collegiate vibes. The combination feels effortless and cute, while still offering layering potential for cold days. Perfect for relaxed weekends or study sessions at a favorite café, it’s equal parts practical and pretty.
19. Burgundy Wool Coat with Black Turtleneck Dress and Knee-High Boots
This ensemble oozes sophistication. The deep burgundy wool coat adds rich color and warmth, while the black turtleneck dress and boots keep it sleek and refined. Ideal for workdays, dinners, or winter gatherings, it’s a classic combination that never fails to impress — luxurious, timeless, and effortlessly put-together.
20. Argyle Knit Cardigan with White Pleated Mini Skirt
End on a preppy, nostalgic note with this argyle knit cardigan and white pleated mini skirt combo. The retro pattern adds visual charm, while the skirt keeps the look light and playful. Perfect for a crisp winter day out, it’s a stylish nod to vintage fashion that still feels modern and cozy.
Conclusion
Winter skirts bring endless opportunities for creativity and expression — from soft knits to structured layers, each outfit tells its own cozy, stylish story. Whether you’re drawn to feminine silhouettes, tailored outerwear, or nostalgic textures, these 20 winter skirt outfits prove that warmth and elegance can beautifully coexist. Step into the season with confidence, and let your style shine through every layer.
