15 Skirt Going Out Outfit Winter: Chic, Warm & Stylish Looks

Winter nights don’t have to stop you from rocking your favorite skirts—especially when you’re heading out and want to look cute, stylish, and confident. Many people assume skirts and cold weather don’t go together, but winter outfits give you incredible styling options: layering, mixing textures, combining warm fabrics, and creating effortlessly chic looks that feel both fashionable and functional. Skirt outfits are perfect for winter nights out because they let you express your style while giving you endless combinations—from cozy knits to sleek leather, fleece-lined tights, tall boots, and beautiful coats.

Whether you’re dressing for a date night, dinner with friends, a holiday party, or a casual winter weekend outing, skirts can be the foundation of a gorgeous winter look. The trick is choosing the right fabrics, pairing the right layers, and balancing warmth with aesthetic. This guide gives you 15 complete skirt going out outfit winter ideas that are warm, trendy, and completely wearable. Each idea includes a detailed explanation to help you recreate the look effortlessly.

Before diving into the outfit ideas, let’s start with a few winter must-have items that make any skirt outfit work, no matter how cold it gets.

5 Items to Buy for Winter Skirt Outfits

These essentials will elevate your winter skirt looks while keeping you warm and stylish.

1. Fleece-Lined Tights

Warm, soft, and comfortable, fleece-lined tights allow you to wear mini, midi, or even slit skirts during winter without freezing. Choose neutral colors like black, gray, or brown so they match almost everything. They maintain insulation while giving you a smooth, polished look under your skirt. Perfect for nights out where you want warmth without bulk.

2. Knee-High or Over-the-Knee Boots

Boots are the backbone of winter skirt outfits. Knee-high boots add structure, elegance, and warmth, while over-the-knee boots bring drama and coverage. They pair beautifully with mini skirts and help elongate your legs. Look for leather or suede versions for maximum winter durability.

3. A Tailored Wool Coat

A high-quality wool coat instantly elevates any skirt outfit. Whether long, midi, or structured, it adds sophistication and warmth. Choose colors like camel, black, navy, or gray for versatility. Wool coats complement skirts wonderfully and create a balanced silhouette perfect for going-out looks.

4. Chunky Knit Sweaters

Cozy yet chic, chunky knit sweaters pair amazingly with skirts. Tuck the front into a skirt for shape or layer them over a fitted top. They add texture and contrast—especially when styled with leather skirts, satin skirts, or pleated skirts. A great sweater makes your winter look both soft and stylish.

5. Leather Mini or Midi Skirt

Leather skirts are winter staples. They’re warm, structured, and perfect for going out. A black leather skirt fits everything—from turtlenecks to cropped jackets to oversized coats. It’s the most versatile skirt type for winter nights out, giving you a sleek, polished vibe.

How to Style Skirts for Winter Going Out Looks

Skirts are incredibly adaptable during winter when styled with the right balance of fabrics, layers, and accessories. Focus on warmth through tights, boots, long coats, and insulated tops, and let the skirt elevate your look with shape, color, or texture. Whether you’re choosing a mini, midi, pleated, or fitted skirt, winter styling opens the door to endless combinations.

15 Skirt Going Out Outfit Winter Ideas

1. Leather Mini Skirt with Turtleneck and Long Wool Coat

A leather mini skirt paired with a fitted turtleneck is one of the chicest winter going-out looks. The turtleneck adds warmth while the leather skirt brings structure and sleekness. Add fleece-lined tights and knee-high boots for extra insulation. Finish the outfit with a long wool coat that ties everything together for an effortlessly elegant winter night out. This look works well for dinner dates, rooftop lounges, or casual winter parties.

2. Satin Midi Skirt with Chunky Knit Sweater

Winter is the perfect season to mix textures, and a satin midi skirt paired with a chunky knit sweater creates a soft, romantic look. The shiny satin contrasts beautifully with the cozy sweater, making the outfit visually interesting. Add ankle boots or pointed-toe heeled boots to elevate the silhouette. This look is ideal for evenings where you want to feel feminine yet warm, giving you a polished vibe without sacrificing comfort.

3. Pleated Skirt with Faux Fur Jacket

Pleated skirts bring movement and elegance, especially when styled with a warm faux fur jacket. This outfit adds winter glamour without feeling overdone. A fitted top under the jacket balances the volume of the pleated skirt. Heeled boots help elongate the frame and keep the outfit evening-ready. It’s a beautiful choice for holiday outings, romantic nights, or winter events where you want to feel elevated and chic.

4. Wool Mini Skirt with Oversized Sweater

A wool mini skirt is naturally warm, making it perfect for going out during winter. Paired with an oversized sweater, the look becomes comfy yet stylish. The mix of proportions—fitted mini and relaxed top—creates an effortless street-style aesthetic. Add tights and chunky boots or knee-high boots depending on the level of warmth you need. This outfit works for casual evenings, movie nights, or days transitioning into nighttime outings.

5. Wrap Midi Skirt with Fitted Long-Sleeve Top

Wrap skirts create a flattering silhouette for all body shapes. A winter wrap midi skirt paired with a fitted long-sleeve top gives a polished, elegant look. Choose wool or knit wrap skirts for warmth. Add heeled boots and a structured coat for a clean, sophisticated winter look. This outfit is perfect for dinners, work-related events, or dressier nights out when you want a balance of comfort and refinement.

6. Leather Midi Skirt with Statement Blouse

A leather midi skirt adds automatic sophistication, especially when styled with a statement blouse—whether satin, organza, or lace-trimmed. This creates a bold winter going-out outfit that’s both stylish and expressive. Choose tall boots to maintain warmth. Add a sleek coat or cropped jacket depending on the style you want. This is great for birthday dinners, holiday parties, or upscale winter nightlife.

7. Tweed Mini Skirt with Button-Up Shirt and Coat

Tweed is a perfect winter fabric because it’s warm, textured, and timeless. Pair a tweed mini skirt with a crisp button-up shirt for a polished preppy look. Add tights, loafers with socks, or knee-high boots depending on your preference. A long coat in a neutral shade completes the outfit beautifully. This look is perfect for dinners, casual winter dates, and outings where you want a classic yet modern feel.

8. Knit Midi Skirt with Matching Knit Top

A knit matching set is cozy, flattering, and extremely stylish. A knit midi skirt paired with a matching top creates a seamless look that feels both classy and comfortable. The outfit hugs your shape while providing warmth, making it ideal for winter going out nights. Add heeled boots and a structured coat to complete the look. This is an excellent choice for minimalists who love refined winter outfits.

9. Sequined Skirt with Black Turtleneck

A sequined skirt is the star of any winter event. Pair it with a simple black turtleneck to balance the sparkle and keep the focus on the skirt. Wear black tights and heeled boots for extra warmth and sleekness. A faux fur coat adds luxury, making the outfit perfect for New Year’s events, winter parties, or glamorous nights out. This look is festive, eye-catching, and seasonally appropriate.

10. Plaid Mini Skirt with Shearling Jacket

Plaid skirts are winter staples. Paired with a shearling-lined jacket, you get a warm and stylish combination perfect for casual winter nights out. Wear a fitted top underneath to maintain balance. Add tights and chunky boots for warmth and edge. This outfit has a youthful, trendy feel and works beautifully for café dates, night walks, or winter markets.

11. Slit Midi Skirt with Cropped Sweater

Slit skirts add subtle allure even in winter. Pair a slit midi skirt with a cropped sweater for a modern silhouette. The cropped top highlights the waist while the longer skirt keeps you warm. Add high boots and a tailored coat for a chic touch. This is a great outfit for evenings where you want something slightly dressy but still comfortable and warm.

12. Velvet Mini Skirt with Long-Sleeve Bodysuit

Velvet is naturally warm and luxurious, making it perfect for winter skirt outfits. Pair a velvet mini skirt with a long-sleeve bodysuit for a sleek, comfortable going-out look. Add tights and heeled boots to elevate the outfit. A faux fur or wool coat finishes the look with sophistication. This is an excellent choice for winter dinners, gatherings, and festive events.

13. High-Waisted Skirt with Off-the-Shoulder Sweater

A high-waisted skirt paired with an off-the-shoulder sweater creates a beautiful winter look that’s subtly flirty yet warm. The off-the-shoulder detail adds elegance, while the high waist shapes the body. Choose a midi skirt for warmth. Add heeled boots and a shawl-style coat to complete the outfit. It’s perfect for date nights or romantic evenings.

14. Maxi Skirt with Fitted Turtleneck and Belt

Maxi skirts provide more coverage, making them excellent for winter. Pair a flowy or pleated maxi skirt with a fitted turtleneck and cinch the waist with a belt for a stunning silhouette. Add heeled boots to elongate your frame. A long coat enhances the outfit’s elegance. This is ideal for dressy winter outings where comfort meets sophistication.

15. Faux Leather Skirt with Cropped Jacket

For a modern and trendy winter look, pair a faux leather skirt with a cropped jacket—like a puffer, shearling, or moto jacket. Wear a fitted top underneath to balance the layers. Add tights and boots for warmth. This outfit is edgy, bold, and perfect for nightlife, concerts, and fun outings where you want to stand out.

FAQ

How do I stay warm while wearing a skirt in winter?

Layering is key: fleece-lined tights, tall boots, warm fabrics like wool and leather, and long coats will keep you warm without compromising style.

Which skirt length is best for winter going out outfits?

Mini, midi, and maxi skirts all work—just style them correctly. Midis are most popular because they offer warmth and elegance.

Can I wear open-toe shoes with skirt winter outfits?

It’s better to stick to boots or closed-toe shoes during winter for warmth and comfort, especially during cold nights out.

Are leather skirts good for winter?

Yes, leather skirts are warm, durable, and stylish—making them one of the best skirt options for winter.

What tops work best with winter skirt outfits?

Turtlenecks, chunky sweaters, fitted long-sleeve tops, bodysuits, and statement blouses all work beautifully depending on the occasion.

Final Words

Winter doesn’t mean sacrificing style—and skirts prove it. With the right layers, fabrics, and accessories, you can create chic, warm, and fashion-forward going-out outfits all season long. These 15 skirt going out outfit winter ideas are designed to help you feel confident, cozy, and effortlessly stylish no matter where your night takes you. Experiment with textures, play with proportions, and enjoy the versatility that skirts bring to winter fashion.