Winter doesn’t mean you have to give up skirts. With the right layering, textures, and silhouettes, skirts can be some of the most versatile pieces in your cold-weather wardrobe. From cozy knits to structured coats, these winter skirt outfits will help you stay warm while looking polished, feminine, and stylish all season long.
Below, you’ll find 20 curated outfit ideas designed for real life — work, weekends, casual days, and holiday gatherings. Each look balances practicality and style so you can feel comfortable without compromising on aesthetics.
20 Stylish Winter Skirt Outfits to Stay Warm & Chic
Black oversized blazer + White Pleated Maxi Skirt + Bright Accessories
A black oversized blazer adds structure and a modern, relaxed silhouette. Pairing it with a white pleated maxi skirt creates a soft contrast that feels elegant yet effortless. The movement of the pleats balances the blazer’s volume, keeping the look refined instead of bulky. Adding bright accessories brings a pop of color and personality, making the outfit feel fresh and winter-appropriate without losing its minimal chic vibe.
Light-gray sweatshirt layered over a white button-down shirt + black full A-line skirt + minimal accessories
Layering a light-gray sweatshirt over a crisp white shirt gives this outfit a relaxed yet polished foundation. The black full A-line skirt adds volume and movement, balancing the casual top with a more structured, elegant bottom. Keeping accessories minimal helps maintain the clean, modern feel of the look. This pairing is comfortable enough for everyday wear while still feeling refined and intentional.
White Bouclé Short Jacket + White Full Midi Skirt + Soft-Tone Accessories
A white bouclé short jacket brings texture and a polished winter feel. Paired with a white full midi skirt, the look feels elegant, cohesive, and softly dimensional. Soft-tone accessories — like beige, blush, or pearl accents — maintain the outfit’s feminine and gentle aesthetic. This is a perfect winter outfit for daytime events, weekend outings, or anywhere you want a refined but approachable look.
Light Gray oversized Sweatshirt + Light-blue Denim Slit Maxi Skirt + Wide Belt
A light gray oversized sweatshirt creates a relaxed, cozy top half that balances beautifully with the structure of a denim slit maxi skirt. The front or side slit adds movement and prevents the outfit from looking too heavy for winter. A wide belt defines the waist, pulling the loose silhouette together and adding a polished focal point. This look blends comfort and shape, making it perfect for casual winter days when you still want to look intentional.
Pink V-Neck Knit + White Straight Maxi Skirt + Black Accessories
A pink V-neck knit brings softness and a touch of winter brightness. The white straight maxi skirt keeps the outfit clean and elongating. Black accessories add contrast, grounding the lighter colors and giving the look a refined finish. This is a gentle, feminine winter outfit that feels both cozy and polished.
Taupe Shearling Jacket + Black Straight Maxi Skirt + Matching Inner Layer
A taupe shearling jacket adds winter texture and instant warmth. The black straight maxi skirt provides structure and tones down the heaviness of the outer layer. A matching inner layer helps unify the look and keeps the palette cohesive. This outfit blends practicality and style — perfect for cold days when you still want a refined silhouette.
Dark Gray Fuzzy Jacket + Blue-and-White Plaid Maxi Skirt + Minimal Accessories
A dark gray fuzzy jacket offers soft texture and winter comfort. The blue-and-white plaid skirt adds pattern and movement, creating a balanced contrast with the plush top. Minimal accessories keep the look uncluttered and everyday-friendly. Great for relaxed winter outings or casual gatherings.
Plaid Mini Skirt + Chunky Knit Sweater + Opaque Tights + Knee-High Boots
A plaid mini skirt brings a festive, retro touch to winter styling. A chunky knit sweater adds cozy volume and balances the skirt’s shorter length. Opaque tights keep legs warm, while knee-high boots elongate the frame and add polish. Great for casual holiday gatherings.
Leather Pencil Skirt + Cashmere Crewneck + Trench Coat + Loafers
A leather pencil skirt offers a subtle edge while still feeling refined. A cashmere crewneck sweater softens the leather’s sharpness and ensures warmth. A classic trench coat layered on top adds elegance. Loafers complete the look with a smart, minimalist finish.
Satin Midi Skirt + Turtleneck + Faux Fur Coat + Heeled Boots
A satin midi skirt introduces a bit of shine and femininity. Balanced by a snug turtleneck, it avoids being too delicate for winter. A faux fur coat adds luxury and warmth. Heeled boots elevate the ensemble, making it perfect for holiday dinners or winter parties.
Denim Skirt (Midi) + Cashmere Sweater + Oversized Wool Coat + Sneakers
A midi denim skirt is a versatile winter option that feels relaxed yet put-together. A cashmere sweater softens the look while keeping cozy. An oversized wool coat adds structure and warmth. Sneakers keep it casual — suitable for daytime errands or coffee dates.
Pleated Midi Skirt + Mock Neck Top + Blazer + Ankle Boots
A pleated midi skirt brings movement and femininity to winter outfits. A fitted mock-neck top offers warmth and a clean silhouette. Throw on a structured blazer for a refined, slightly formal layer. Ankle boots round out the look — perfect for work or smart casual occasions.
Tweed Pencil Skirt + Button-Down Shirt + Long Coat + Classic Pumps
A tweed pencil skirt adds texture and vintage charm. A crisp button-down shirt brings structure and sophistication. A long coat completes the layered winter look. Classic pumps finish the outfit, making it appropriate for office meetings or formal winter events.
Wool Wrap Skirt + Turtleneck + Belted Overcoat + Knee Boots
A wool wrap skirt offers adjustable comfort and an elegant drape. A turtleneck provides a warm, streamlined upper half. Layering a belted overcoat accentuates the waist and adds polish. Knee boots ensure warmth and complete the chic winter silhouette.
Velvet Mini Skirt + Thermal Top + Chunky Cardigan + Tights + Booties
A velvet mini skirt gives a festive, luxurious feel — perfect for holiday parties. A thermal top keeps warmth without bulk. A chunky cardigan layered over adds cozy texture. Tights and booties make the outfit winter-ready and balanced.
Checked Midi Skirt + Wool Sweater + Scarf + Chelsea Boots
A checked midi skirt offers pattern and seasonal charm. A wool sweater keeps the outfit cozy and soft. Adding a scarf brings warmth and visual interest. Chelsea boots add structure and polish, making this a great everyday winter look.
Wool Pleated Mini Skirt + Oversized Knit + Long Wool Coat + Mary Jane Shoes
A wool pleated mini skirt balances softness and structure. An oversized knit adds comfort and winter-ready texture. A long wool coat provides warmth and polish. Mary Jane shoes add a subtle retro charm — perfect for cozy winter brunches or casual holiday meetups.
Knit Maxi Skirt + Layered Sweaters + Belt + Tall Boots
A knit maxi skirt provides maximum warmth and a fluid shape. Layering sweaters brings texture and comfort. Adding a belt defines the waist under heavy layers. Tall boots complete the look, keeping legs warm and elongating the silhouette.
Tweed A-Line Skirt + Fine Knit Sweater + Wool Blend Coat + Loafers
A tweed A-line skirt adds classic texture and sophistication. A fine knit sweater keeps the upper half warm without bulk. A wool-blend coat provides a polished layer that ties everything together. Loafers maintain a refined but comfortable finish.
Leather Midi Skirt + Thermal Tee + Oversized Cardigan + Chunky Boots
A leather midi skirt combines edge with winter appropriateness. A thermal tee keeps the base warm and simple. An oversized cardigan softens the leather and adds cozy layers. Chunky boots give both warmth and balance — perfect for cold-weather street style.
Conclusion
Skirts are far from off-limits in winter — with the right combinations of layers, textures, and footwear, they become a versatile base for both cozy casual looks and polished outfits. Mixing materials like wool, velvet, leather, and knitwear helps achieve warmth without sacrificing style.
Whether you lean toward feminine elegance, casual comfort, or edgy chic, these 20 winter skirt outfits offer plenty of inspiration for cold-season wardrobes.
