Winter is here, and you’re looking to stay cozy while keeping your style on point. Flared leggings are a game-changer for the colder months, offering the comfort of leggings with a chic twist.
But, how do you make them work for winter outfits? Finding the right combinations can be tricky, especially when you want warmth without sacrificing style.
In this guide, we’ll explore flared leggings winter outfit ideas that bring both comfort and flair to your wardrobe. Let’s unlock the secret to stylish winter dressing with the trend you didn’t know you needed.
21 Stylish Flared Leggings Winter Outfit Ideas to Keep You Cozy and Chic
#1. Cozy Winter Chill Outfit
When comfort meets style, this cozy look is a winner. A soft, oversized sweater with a light argyle print pairs effortlessly with high-waisted flared leggings, creating a laid-back yet trendy silhouette. The white long-sleeve shirt underneath adds warmth without bulk, while the classic white sneakers ground the look with a casual vibe. A light and cozy winter outfit perfect for indoor lounging or casual outings.
The chunky sweater’s subtle pattern contrasts nicely with the black flared leggings, adding texture and style. White sneakers and a simple, relaxed fit make this ensemble ideal for a day spent at home or a relaxed winter stroll.
#2. Street Style Relaxation
Effortless style meets comfort with this casual yet chic outfit. A loose white hoodie adds a relaxed vibe, while the high-waisted black flared leggings elongate the legs, creating a flattering silhouette. White sneakers add a sporty touch, and the small handbag gives the look just the right amount of structure.
This easy-going outfit is perfect for a coffee run or casual weekend outings. This cozy yet fashionable look combines a soft oversized hoodie with sleek black flared leggings, ideal for urban strolling or grabbing a drink with friends. The sneakers and compact bag complete the ensemble with comfort and practicality.
#3. Sunlit Casual Vibes
A carefree, casual vibe defines this look. The loose white t-shirt flows over the high-waisted black leggings, creating a laid-back silhouette. Paired with white sneakers, this outfit is perfect for a sunny afternoon walk.
The natural sunlight reflects off the surroundings, adding to the relaxed feel of the outfit. Light and easy, this simple white t-shirt paired with black flared leggings is a warm-weather favorite. The white sneakers keep it fresh and sporty, while the relaxed fit is perfect for a laid-back outdoor outing or a casual gathering.
#4. Earthy Brown Day Out
Embrace the earthy tones with this comfy yet stylish look. A soft cream-colored ribbed top tucked into high-waisted brown flared leggings creates a chic, balanced ensemble. White platform sneakers add a pop of brightness while giving the outfit a modern edge.
This outfit is perfect for a casual day out in nature or a relaxed weekend brunch. A blend of cozy comfort and stylish flair, this brown ribbed top and flared leggings set is ideal for any laid-back outing. The white sneakers enhance the casual, earthy tones while ensuring maximum comfort for all-day wear.
#5. Chill and Cozy Lounging
Simple yet stylish, this gray sweatshirt paired with matching high-waisted flared leggings creates a perfect lounging look. The oversized fit of the sweatshirt adds comfort, while the sleek leggings offer a touch of sophistication. Whether you’re hanging out at home or grabbing coffee, this outfit is all about cozy vibes.
The relaxed fit of this gray sweatshirt paired with matching flared leggings is perfect for a day of comfort. Casual and laid-back, the outfit ensures style without sacrificing warmth, making it ideal for indoor or outdoor activities on a chilly day.
#6. Edgy Urban Layering
Styled with a cool, edgy vibe, this look features a black leather jacket layered over a sleek, fitted black top. The black flared leggings flow effortlessly to pair with chunky black boots, enhancing the street-style appeal. A simple yet chic bag adds functionality without compromising the outfit’s bold aesthetic. A bold, street-inspired ensemble perfect for a casual day out.
The leather jacket adds toughness, while the black flared leggings keep the look feminine and flattering. Chunky boots and a crossbody bag elevate the overall cool, laid-back vibe.
#7. Vibrant Comfort Vibes
A comfy oversized sweatshirt in a bright green hue instantly brings a cheerful touch to this outfit. Paired with classic black flared leggings and white sneakers, the outfit combines comfort with vibrant energy.
Perfect for a day spent exploring or running errands. This cozy sweatshirt and black flared leggings combo is both fun and functional. The bold color of the sweatshirt contrasts beautifully with the sleek leggings, creating a stylish yet relaxed vibe that’s perfect for an on-the-go look.
#8. Holiday Warmth
This festive holiday outfit combines warmth and style effortlessly. A cozy, patterned sweater in rich reds and blues is paired with high-waisted red flared leggings. The comfy boots keep you cozy for winter outings.
Ideal for the holidays, this red and blue sweater paired with flared leggings gives off a cheerful, cozy vibe. The soft boots complete the look for winter fun, whether you’re enjoying a Christmas gathering or a holiday shopping trip.
#9. Modern Minimalist Charm
A crisp black cropped top paired with black high-waisted flared leggings creates a sleek silhouette that oozes modern charm. A white cardigan adds a soft layer, while white sneakers add the right balance of style and comfort. Black-on-black never goes out of style.
The cropped top and leggings combo is effortlessly chic, while the white cardigan brings in a softer, layered look. The white sneakers provide a sporty, fresh twist to this trendy outfit.
#10. Effortless City Stroll
Casual yet cool, this look combines a white cropped hoodie with black flared leggings. The sneakers keep the look sporty and practical while giving it a sleek finish. With an iced coffee in hand and a confident smile, this outfit is ideal for a laid-back day in the city.
Simple yet stylish, this hoodie and black flared leggings combo is a great option for city adventures. The white sneakers add to the relaxed feel, while the cozy hoodie ensures comfort for all-day wear.
#11. Soft Beige Relaxation
Styled in neutral tones, this beige oversized sweatshirt perfectly complements the black flared leggings. The casual vibe is elevated with a pair of white sneakers, making this outfit a great choice for errands or a chilled-out weekend hangout.
Cozy and chic, this oversized beige sweatshirt and black flared leggings combo brings a laid-back yet trendy look. The soft neutrals keep it casual, while the white sneakers add a crisp touch to the outfit.
#12. Cozy Street Style
Embrace the winter chill with this cozy layered look. A beige fleece jacket paired with a bright green scarf adds color and warmth to the outfit, while the black flared leggings and pink sneakers ensure comfort during a stroll through the city.
A perfect blend of warmth and style, this outfit combines a soft fleece jacket with vibrant accessories. The black flared leggings provide flexibility, while the sneakers add a modern twist to the cozy ensemble.
#13. Sophisticated City Walk
Minimalistic and polished, this black oversized hoodie paired with black flared leggings offers a sleek look. A designer handbag and chic sneakers elevate the vibe, making this outfit perfect for an easygoing day out in the city.
Bold and understated, this all-black look with a designer bag is perfect for a stylish city walk. The oversized hoodie adds comfort, while the sleek sneakers keep it fresh and chic for any occasion.
#14. Classy Street Elegance
With a chic beige blazer draped over a simple black top, this look mixes sophistication with comfort. The black flared leggings give the outfit a modern touch, while black pointed flats make the look polished and ready for a stylish day out.
Combining structure and flow, this beige blazer and black flared leggings set is ideal for a classy yet comfortable day out. The pointed flats and minimal accessories keep the vibe sleek and elegant, perfect for an afternoon in the city.
#15. Casual Chic Coffee Run
A stylish look for a coffee run or casual outing, this cozy white hoodie is layered with a beige jacket, creating a perfect balance between warmth and style. Paired with black flared leggings and white sneakers, this outfit is both comfortable and effortlessly cool.
A chic, casual outfit ideal for chilly mornings. The white hoodie and beige jacket combo provides warmth, while the black flared leggings give it a sleek silhouette. White sneakers complete the comfortable, laid-back look.
#16. Seaside Casual Vibes
This bold, green oversized sweatshirt with “EMPATHY” written across adds a playful and youthful vibe to the outfit. Paired with black flared leggings and white sneakers, it’s a cool, comfortable choice for a day by the sea or a casual hangout with friends.
Full of vibrant energy, this green oversized sweatshirt is paired with sleek black flared leggings for a relaxed yet stylish look. White sneakers keep the outfit grounded, and the seaside backdrop adds to the carefree vibe.
#17. Sleek Winter Elegance
This stylish black ensemble with a tailored coat and structured bag creates a sophisticated winter look. The black flared leggings paired with shiny black boots add edge, while the structured handbag completes the outfit with class.
A chic winter outfit combining sleek black flared leggings with a tailored coat and elegant accessories. The black boots and handbag bring sophistication to the casual style, perfect for winter outings in the city.
#18. Cozy Winter Chic
A classic oversized puffer jacket layered over a purple sweater adds comfort and warmth to this stylish winter outfit. Paired with black flared leggings and white sneakers, the ensemble stays practical while looking effortlessly chic.
This cozy yet trendy look pairs a puffer jacket with a pop of purple and sleek black flared leggings. White sneakers complete the outfit, making it ideal for a day of comfort and style during chilly winter months.
#19. Cozy Neutral Comfort
This warm, beige knitted sweater adds an instant cozy vibe, pairing perfectly with black flared leggings for a balanced silhouette. White sneakers provide a touch of freshness, and the laid-back pose completes the effortless look. Ideal for a relaxed day at home or a casual outing.
Effortlessly stylish, this beige sweater and black flared leggings combo creates a cozy, comfy outfit. Paired with white sneakers, it’s the perfect choice for a casual, chic day, offering comfort with a fashionable twist.
#20. Urban Explorer
A casual yet stylish outfit, this white crop top and black flared leggings bring an urban edge. Paired with silver sneakers and a small black bag, this look is perfect for strolling the city streets while feeling comfortable and chic.
A minimalist, street-style outfit that combines a white crop top with black flared leggings. The silver sneakers and sleek bag add to the cool, laid-back vibe, making it an ideal choice for a day of city exploration.
#21. Playful Checkered Fun
This look captures the perfect blend of casual and playful. A denim jacket adds structure, while a checkered hat injects a bit of fun into the outfit. Paired with black flared leggings and white sneakers, this look is perfect for a day at the amusement park or a day out with friends.
Fun and fashionable, this denim jacket and checkered hat combo pairs perfectly with black flared leggings. The white sneakers add a fresh twist to the look, making it ideal for casual outings with a playful touch.
