Introduction
Winter fashion doesn’t mean saying goodbye to your favorite skirts—it just means styling them smarter. With the right layers, textures, and accessories, skirts can be your go-to statement piece even in chilly weather. Think plush knits, structured wool, cozy tights, and boots that make braving the cold a stylish affair. Whether you’re heading to the office, enjoying a snowy city stroll, or dressing up for a holiday gathering, winter skirt outfits let you blend femininity with function.
In this guide, you’ll discover 25 Winter Skirt Outfits that balance warmth and trendiness. From casual weekend looks to sophisticated dinner ensembles, each idea is tailored to inspire your seasonal wardrobe. Ready to make your winter skirts the star of your closet? Let’s dive in.
1. Wool A-Line Skirt + Turtleneck Sweater
A classic wool A-line skirt pairs beautifully with a fitted turtleneck for a timeless winter look. Add opaque tights and ankle boots for extra warmth. Finish with a long wool coat and a structured handbag for city-ready polish. Choose deep jewel tones like emerald or burgundy for a seasonal pop.
2. Midi Pleated Skirt + Oversized Knit
Balance the flow of a pleated midi skirt with the cozy volume of an oversized chunky sweater. Tuck in the front for shape, then add tall leather boots. A belted waistcoat or blazer can elevate the look for work or a winter brunch date.
3. Corduroy Mini Skirt + Thermal Tights
Corduroy adds texture and warmth, making it perfect for winter minis. Wear with thick thermal tights, a ribbed turtleneck, and knee-high boots. Layer a shearling jacket over the top for retro-cool winter vibes.
4. Knit Pencil Skirt + Matching Sweater Set
Go monochrome with a ribbed knit pencil skirt and matching sweater. This coordinated look feels elegant yet effortless. Pointed-toe ankle boots and a wool wrap coat complete the outfit, perfect for office days or dinner reservations.
5. Leather Skirt + Cashmere Sweater
A leather skirt instantly adds edge to winter dressing. Style it with a soft cashmere sweater for a high-low contrast. Add opaque tights, lace-up boots, and a tailored coat for a chic city stroll ensemble.
6. Tweed Skirt + Button-Up Shirt + Sweater Vest
Layer a crisp button-up under a sweater vest and pair with a tweed skirt for a preppy winter aesthetic. Loafers and wool socks work for milder days, while tights and ankle boots are great for colder temps.
7. Maxi Skirt + Fitted Turtleneck + Belt
Flowy maxi skirts work in winter with heavier fabrics like wool or corduroy. Cinch your waist with a belt, wear a fitted turtleneck, and finish with block-heeled boots. A cropped puffer adds a modern touch.
8. Satin Midi Skirt + Cable-Knit Sweater
For winter evenings, style a satin midi skirt with a chunky cable-knit sweater. The mix of soft sheen and cozy knit creates contrast. Add heeled ankle boots and a faux-fur stole for extra glamour.
9. Plaid Skirt + Oversized Coat
Nothing says winter like plaid. Pair a plaid skirt with a fitted knit top and a dramatic oversized coat. Finish with knee-high boots and a beret for a French-inspired cold-weather look.
10. Denim Skirt + Longline Cardigan
Yes, denim skirts work in winter! Choose a dark wash midi, layer with a thermal top, and add a chunky longline cardigan. Finish with fleece-lined tights and lug-sole boots for casual comfort.
11. Velvet Skirt + Blouse + Blazer
Velvet’s rich texture shines in winter. Pair a velvet skirt with a silky blouse and tailored blazer for a dinner-ready look. Add sheer black tights and pointed heels for an elegant finish.
12. Asymmetrical Hem Skirt + Slim Sweater
An asymmetrical skirt adds movement and intrigue to winter looks. Style with a slim-fit sweater, opaque tights, and ankle boots. A belted coat keeps the outfit sleek and structured.
13. Maxi Knit Skirt + Cropped Puffer
Go sporty-chic with a maxi knit skirt, slim turtleneck, and cropped puffer jacket. Sneakers keep it casual, while heeled boots dress it up. Opt for neutral tones for minimal winter vibes.
14. Metallic Skirt + Black Turtleneck
A metallic skirt brings holiday sparkle to winter outfits. Keep it balanced with a simple black turtleneck, opaque tights, and classic pumps or ankle boots. Great for parties and seasonal events.
15. Button-Front Skirt + Chunky Scarf
Choose a button-front wool skirt, layer with a knit top, and wrap yourself in an oversized chunky scarf. Add lace-up boots and a crossbody bag for a cozy yet stylish day look.
16. Mini Skirt + Over-the-Knee Boots
Combat the chill with over-the-knee boots that cover most of your legs while still letting a mini skirt peek through. Pair with a fitted turtleneck and structured coat for a sleek silhouette.
17. Wrap Skirt + Layered Sweaters
Wrap skirts in heavier fabrics like wool are perfect for winter layering. Wear a thin knit base, top with a chunky cardigan, and finish with ankle boots. Add a beret for a Parisian twist.
18. Tulle Skirt + Fitted Knit
Tulle skirts aren’t just for summer—layer a winter tulle skirt with a fitted knit sweater, tights, and block-heel ankle boots. Add a tailored coat for a whimsical yet polished look.
19. Skater Skirt + Hoodie + Coat
For a casual streetwear vibe, pair a skater skirt with a hoodie and oversized wool coat. Chunky sneakers or combat boots keep it cool. Add a beanie for an extra laid-back touch.
20. Plaid Pleated Skirt + Sweater + Leather Jacket
Mix textures by pairing a plaid pleated skirt with a cozy sweater and a sleek leather jacket. Finish with ankle boots and layered necklaces for a bold, edgy winter look.
21. Maxi Slip Skirt + Knit Wrap Top
Transform a silky slip skirt into a winter staple by pairing it with a knit wrap top. Add heeled boots and a wool coat for date nights or upscale dinners.
22. Corduroy Midi Skirt + Henley + Shacket
Corduroy midis are perfect for casual winter days. Pair with a henley top, layer a plaid shacket, and finish with lace-up boots. Add a knit beanie for extra warmth.
23. Tiered Skirt + Fleece-Lined Leggings
Keep wearing your tiered skirts by layering fleece-lined leggings underneath. Add a chunky knit sweater and ankle boots. A parka jacket ensures maximum warmth without sacrificing style.
24. Pencil Skirt + Blouse + Long Coat
For workwear, style a wool pencil skirt with a silk blouse and a tailored long coat. Add heeled boots or loafers, and choose muted tones for an office-friendly winter aesthetic.
25. Pleated Mini Skirt + Cropped Sweater
Finish with a playful combo—a pleated mini skirt and cropped sweater layered over a thermal top. Pair with thick tights and chunky boots. Great for weekend outings and coffee runs.
Conclusion
With the right layers and textures, skirts can shine even in the coldest months. These Winter Skirt Outfits prove you can stay warm without sacrificing style—whether it’s wool minis, flowing maxis, or statement midis. Mix and match these looks, experiment with textures, and don’t forget your winter essentials like thermal tights, gloves, and a cozy scarf. Which outfit will you try first? Save this guide for your next seasonal wardrobe refresh.
