12 Black Flared Leggings Outfit Winter Looks That Trend Now
You’ve probably noticed black flared leggings dominating winter street style, and there’s good reason why they’re everywhere right now. These versatile pieces effortlessly bridge the gap between comfort and sophistication, creating that coveted elongated silhouette while keeping you warm during colder months. From cozy oversized sweaters to edgy combat boot combinations, the styling possibilities seem endless. But here’s what most people don’t realize about maximizing their potential this season.
Oversized Sweater and Knee-High Boots Combo

Nothing beats the cozy elegance of pairing black flared leggings with an oversized sweater and knee-high boots for winter styling. This combination creates the perfect balance between comfort and sophistication that lets you move freely while looking effortlessly put-together.
The oversized sweater provides essential cozy layering that keeps you warm without restricting movement. Choose chunky knits in neutral tones like cream, camel, or soft gray to complement your black flared leggings.
Knee-high boots elongate your silhouette while adding structure to the relaxed sweater silhouette. For chic accessorizing, add a structured crossbody bag and delicate jewelry. Layer a long pendant necklace over your sweater for visual interest.
Complete the look with a wool scarf in a contrasting texture to enhance the cozy-meets-chic aesthetic that defines modern winter fashion. These versatile winter styling combinations work seamlessly for both casual outings and more polished occasions throughout the colder months.
Cropped Puffer Jacket With Chunky Sneakers

The versatility of athletic-inspired fashion shines when you combine black flared leggings with a cropped puffer jacket and chunky sneakers for winter street style. This trend-forward combination gives you the freedom to move comfortably while staying warm and stylish throughout cold weather months.
Choose a cropped puffer jacket with faux fur trims around the hood for added texture and visual interest. The shorter length perfectly balances your wide leg silhouette without overwhelming your proportions. Pair this with white or cream chunky sneakers to create contrast against your dark leggings. Black leggings serve as the perfect foundation for versatile styling options that can transition from casual to more polished looks.
Layer a fitted turtleneck or thermal top underneath your puffer jacket for extra warmth. Add a crossbody bag and minimal jewelry to complete the look. This outfit works perfectly for casual outings, weekend errands, or coffee dates when you want comfort without sacrificing style.
Long Cardigan and Ankle Boots Pairing

Why settle for basic layering when black flared leggings paired with a long cardigan and ankle boots create an effortlessly chic winter ensemble? This combination gives you complete freedom to move while maintaining sophisticated style throughout colder months.
Choose an oversized knit cardigan in neutral tones like cream, camel, or charcoal for maximum versatility. The flowing silhouette balances your flared leggings’ fitted waistband perfectly.
Stylish layering becomes simple when you add a fitted turtleneck underneath for extra warmth. Ankle boots with block heels provide stability and comfort for all-day wear. Suede or leather options work equally well, depending on your personal preference. This leggings and boots pairing creates a foundation for timeless winter style that never goes out of fashion.
Complete this look through chic accessorizing with a structured crossbody bag and delicate gold jewelry. You’ll achieve an elevated casual aesthetic that shifts seamlessly from coffee runs to dinner dates.
Fitted Turtleneck With Statement Coat

Statement coats alter your fitted turtleneck and black flared leggings combination into a winter ensemble that commands attention wherever you go. The high neck silhouette creates a sleek foundation that pairs beautifully with oversized outerwear pieces like wool coats or faux fur jackets.
Choose bold colors such as emerald green, burgundy, or classic camel to break up winter’s monochrome palette. Your fitted turtleneck should hug your torso without bunching, ensuring clean lines underneath your statement piece.
For professional settings, consider this look layered with blazer underneath your coat for extra warmth and sophistication. The versatility of black flare leggings makes them perfect for transitioning from casual weekend wear to more polished winter occasions. Complete the outfit with knee-high boots or ankle booties in matching black leather. This combination gives you the freedom to express your personal style while staying warm during cold weather months.
Hoodie and Combat Boots Street Style

When you’re aiming for an effortlessly cool street style vibe, oversized hoodies paired with combat boots create the perfect contrast to your black flared leggings’ feminine silhouette. This edgy combination lets you express your rebellious side while staying comfortable and warm during winter months.
Choose an oversized hoodie in neutral tones like gray, cream, or classic black to maintain versatility in your wardrobe. The relaxed fit balances the fitted nature of your leggings perfectly. Combat boot trends currently favor chunky platforms and weathered leather finishes that add instant attitude to any outfit.
Layer a denim or leather jacket over your hoodie for extra warmth and visual interest. These sleek monochrome looks with all-black winter leggings create a cohesive and sophisticated aesthetic that’s perfect for urban environments. Complete the look with a crossbody bag and minimal jewelry to keep the focus on your striking silhouette.
Blazer and Loafers Smart-Casual Look

Elevating your black flared leggings from casual streetwear to workplace-appropriate attire becomes effortless with a structured blazer and polished loafers. This chic blazer pairing adapts your look into sophisticated office wear that doesn’t sacrifice comfort for style.
Choose a customized blazer in neutral tones like navy, charcoal, or cream to create a polished foundation. The structured shoulders and clean lines provide professional balance against the leggings’ relaxed silhouette. Pair with leather or suede loafers in black, brown, or burgundy for refined footwear that maintains comfort throughout your workday.
Office appropriate accessorizing completes this smart-casual ensemble. Add a structured tote bag, delicate jewelry, and a silk scarf for sophisticated touches. This combination gives you the freedom to move confidently between meetings while maintaining professional standards. These winter outfits built around black leggings prove their versatility extends far beyond casual weekend wear.
Cable Knit Sweater and Tall Boots Ensemble

Cozy textures meet winter functionality when you pair black flared leggings with a chunky cable knit sweater and tall boots for an effortlessly stylish cold-weather look. The cable knit texture adds visual interest and warmth, creating perfect balance against the sleek lines of your flared leggings.
Choose oversized sweaters in cream, camel, or forest green to complement your black base. The relaxed fit gives you freedom to move while maintaining that coveted cozy aesthetic. These soft textures create the ultimate foundation for extra-cozy winter styling. Boot height versatility lets you experiment with knee-highs for drama or mid-calf styles for everyday wear.
Tuck your sweater slightly into the waistband to define your silhouette, or leave it loose for maximum comfort. Add a crossbody bag and delicate jewelry to complete this approachable yet put-together winter ensemble that works everywhere.
Denim Jacket Layered With Scarf Accent

Black flared leggings create an unexpected foundation for casual denim styling when you layer a classic jean jacket with a colorful scarf accent. This combination breaks traditional fashion rules while providing effortless winter versatility you’ll love wearing anywhere.
Choose a medium-wash denim jacket that hits at your hip for the most flattering silhouette. Add cozy scarf textures like chunky knits or soft cashmere in vibrant colors that contrast beautifully against the denim’s blue tones. Wrap the scarf loosely around your neck, letting the ends cascade naturally for movement.
Complete this relaxed look with ankle boots and layered necklace accents that peek through the scarf opening. This styling approach gives you freedom to express your personality while staying warm and comfortable throughout your day.
Mock Neck Top With Trench Coat Sophistication

Sophisticated mock neck tops paired with customized trench coats transform black flared leggings into refined winter outfits that function effortlessly from office meetings to dinner dates. You’ll create instant sophistication when you choose neutral-toned mock necks in cream, camel, or soft gray. The high neckline provides warmth while maintaining clean lines that complement your trench coat’s structured silhouette.
This layered look works brilliantly because you’re combining classic pieces that never go out of style. Choose a trench in khaki, navy, or charcoal for maximum versatility. The sophisticated appeal comes from balancing casual flared leggings with enhanced outerwear pieces.
Complete your ensemble with leather ankle boots and a structured handbag. You’ll feel confident knowing this combination shifts seamlessly from professional settings to weekend brunches without compromising comfort or style.
Flannel Shirt and Platform Shoes Combination

Effortless grunge meets heightened comfort when you pair oversized flannel shirts with platform shoes and black flared leggings for winter styling that’s both trendy and practical. This combination breaks fashion rules while creating an unexpectedly polished look that works for casual outings or relaxed work environments.
Choose flannel print patterns in classic buffalo plaid, windowpane checks, or subtle tartans that complement your black leggings without overwhelming your silhouette. Platform heel heights between two to four inches provide the perfect balance of comfort and style elevation, making your flared leggings appear longer and more dramatic.
Layer your flannel over fitted basics, then add chunky jewelry or a crossbody bag to complete the ensemble. This rebellious yet refined approach gives you freedom to express your personality while staying warm and comfortable throughout winter’s unpredictable weather.
Teddy Coat With Minimalist Sneakers

The cozy luxury of teddy coats creates an unexpectedly chic contrast when styled with clean-lined minimalist sneakers and black flared leggings for winter fashion that balances comfort with contemporary appeal. You’ll achieve effortless sophistication by choosing an oversized cream or camel teddy coat that drapes beautifully over your flared silhouette.
The cozy appeal of textured outerwear pairs surprisingly well with streamlined white leather sneakers, creating visual interest through mixed textures. This combination works because you’re mixing high and low elements without sacrificing comfort or style. Choose sneakers with clean lines and minimal branding to maintain the sleek monochrome aesthetic.
Add a structured crossbody bag in black or tan leather to complete the look. This outfit formula lets you move freely through your day while maintaining an augmented appearance that’s both practical and fashion-forward.
Cropped Sweater and Over-the-Knee Boots Statement

While teddy coats offer relaxed comfort, cropped sweaters paired with over-the-knee boots create a bold statement that’s perfect for showcasing your black flared leggings’ silhouette during winter months. This combination gives you complete freedom to express your personal style while staying warm and trendy.
Choose an oversized sweater silhouette that hits just above your hip line, creating visual balance with your flared leggings. The cropped length prevents overwhelming your proportions while maintaining cozy coverage. For over the thigh boot styling, select boots that reach mid-thigh to create an alluring gap between the boot top and sweater hem.
This look works exceptionally well for casual dates, shopping trips, or coffee meetings. You’ll feel confident and stylish while maintaining the comfort you need for winter activities.
Conclusion
You’ve uncovered twelve versatile ways to style black flared leggings this winter season. These outfits prove you don’t need to sacrifice comfort for style during colder months. Mix textures, layer strategically, and choose footwear that complements each look’s vibe. Remember to accessorize thoughtfully with bags, scarves, and jewelry to enhance your ensemble. With these trending combinations, you’ll create effortlessly chic winter outfits that work for any occasion.
