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50+ Winter-Ready Outfits with Cowboy Boots and Leggings

By: Author Grace

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50+ Winter-Ready Outfits with Cowboy Boots and Leggings

Winter is a perfect season to combine warmth, style, and a touch of Western flair with cowboy boots and leggings. These outfits are cozy, practical, and look fantastic against a snowy backdrop.

Here are some outfit ideas to inspire your winter wardrobe, each pairing leggings with cowboy boots for a trendy, comfortable look.

1. Layer up with a deep green wool trench coat, a chunky knit sweater, and brown leather leggings.

This look brings a warm, earthy feel to winter styling, complemented by classic white cowboy boots for a pop of brightness.

The knit gloves add both warmth and a cozy touch, ideal for snowy days.

A woman styled in short white cowboy boots with leather leggings, an oversized olive sweater, and a long trench coat

2. For a playful yet warm look, try a plush white faux fur coat paired with black leggings.

Add a colorful, patterned scarf to bring some contrast and flair, and finish the look with white cowboy boots featuring a touch of red or tan detailing.

This outfit is perfect for strolling through winter markets or festive gatherings, keeping you both warm and stylish.

A woman wears a chic wool coat with a patterned scarf, white cowboy boots, and leggings, posing near a large winter concert stage illuminated with cool-toned lights

3. Embrace ultimate comfort with an oversized, chunky cable-knit sweater in a neutral tone. Pair it with light gray leggings for a soft, monochromatic base.

Light tan cowboy boots blend seamlessly with the winter vibe, creating a cozy, laid-back look that’s perfect for cabin retreats or a walk in the snow.

Full-body image of a woman in a cream-colored chunky knit sweater with leggings in a soft gray tone, paired with tall tan cowboy boots with fringe

4. Go for a relaxed winter look with a long, cozy scarf draped over a thick, oversized sweater.

Dark leggings add contrast, and bright white cowboy boots add a modern twist. This outfit is all about comfort and effortless style, great for casual winter outings with friends or family.

Woman dressed in a casual sweater and scarf, white cowboy boots, and leather leggings, enjoying an outdoor winter concert with stage lights illuminating the cold night

5. Achieve a Western-inspired look by pairing white leggings with a textured cream sweater and a denim jacket with a shearling collar.

White cowboy boots and a white cowboy hat complete the outfit, blending warmth with Western charm.

This look is perfect for winter days when you want to stay comfortable while adding a unique, stylish touch.

Woman in a layered sherpa-lined denim jacket over a knit sweater, white leggings, and white cowboy boots, posing in front of a snow-covered barn

6. Stand out in winter landscapes with a bold red coat over black leggings. The deep red brings festive cheer, while tan cowboy boots keep the look grounded and stylish.

This outfit is easy to pull together yet makes a strong statement, ideal for any winter outing.

Fashion-forward woman in a deep red pea coat, leggings, and tall brown cowboy boots with silver embellishments

7. Go for a soft and feminine winter look with a pastel pink trench coat layered over white leggings.

White cowboy boots add a sleek touch, while the structured coat creates a sophisticated silhouette. This outfit is perfect for a winter brunch or a day out in the city, offering both warmth and style.

A fashion-forward woman with shoulder-length hair wears a pastel pink trench coat over fitted leggings and tall white cowboy boots with minimalistic western designs

8. Stay ultra-warm with a bright red puffer jacket and black leggings. The fitted structure of the leggings balances the bulk of the puffer, while tan cowboy boots bring in that Western vibe.

This look is ideal for those extra cold days when you still want to look stylish and stay comfortable.

A woman in a bright red puffer jacket with black leggings and brown cowboy boots, posing on a snow-covered bench decorated with a holiday wreath

9. For a sophisticated look, go for a double-breasted white coat with black leggings. Pair this outfit with white cowboy boots for a polished, modern vibe.

The simplicity of the colors keeps it chic, perfect for evening outings in the winter.

A woman with an elegant high bun, dressed in a white pea coat, dark leggings, and tall white cowboy boots with clean

10. Stay warm in a light gray puffer jacket, soft gray leggings, and a neutral-toned scarf for added coziness.

Tan cowboy boots keep it grounded with a rustic touch, creating a laid-back winter look. This outfit is ideal for relaxed winter walks or running errands while staying cozy and stylish.

Woman styled in beige cowboy boots, dark gray leggings, and an oversized beige puffer jacket with a knit scarf and gloves

11. Combine classic winter textures with a long plaid coat, a cream turtleneck, and sleek black leather leggings.

The beige cowboy boots add a Western edge to this sophisticated look, while a structured brown handbag completes the ensemble, making it ideal for a day at the lodge or a casual winter outing.

Woman wearing beige cowboy boots, black leather leggings, and a cream turtleneck with a long plaid coat

12. For a warm, cozy outfit, layer an oversized, textured cardigan over a simple winter dress and pair with dark leggings.

Tan cowboy boots add a rustic touch, blending perfectly with the earthy tones of this outfit. This look is soft and comfortable, perfect for a woodland walk on a snowy day.

A stylish woman with shoulder-length brown hair in a thick brown cardigan over a wool dress and leggings, wearing tall tan cowboy boots with silver accents

13. Achieve an effortlessly stylish look by pairing a neutral-toned long coat with black leggings and a chunky beige scarf.

The tan cowboy boots add warmth to the outfit, while the scarf provides extra coziness. This outfit is perfect for exploring holiday markets or enjoying winter festivities in town.

Woman wearing a chunky beige scarf over a long wool coat, black leggings, and brown cowboy boots, walking down a quiet

14. Add a pop of color with a winter coat featuring bold red accents paired with black leggings. Bright red cowboy boots make a statement, contrasting beautifully with the snowy background.

This look is practical and eye-catching, perfect for snowy days when you want to stand out in style.

Woman in a puffy parka with fur trim, black leggings, and red cowboy boots, leaning against a wooden barn surrounded by fresh snow

15. Wrap up in an oversized cardigan in a warm brown shade, layered over a cozy winter dress and brown leggings.

The earthy tones of the tan cowboy boots complete this laid-back, rustic look, ideal for those chilly days when you want to stay warm and comfortable yet stylish.

A stylish woman with shoulder-length brown hair in a thick brown cardigan over a wool dress and leggings

16. For a slightly edgy look, layer a tan leather jacket over a chunky knit turtleneck and black leggings.

The combination of textures gives depth to the outfit, while tan cowboy boots tie in a touch of Western style. This is a perfect winter look for those who want something both cozy and bold.

Woman in a chunky knit sweater under a leather jacket, dark leggings, and tan cowboy boots, posing in a rustic winter setting with frost-covered trees

17. Create a striking look by pairing a tan trench coat with black leggings and a chunky beige turtleneck.

Red cowboy boots add a bold, festive touch, perfect for strolling through city streets decorated for the holidays.

This outfit balances subtle elegance with a pop of color, making it eye-catching yet sophisticated.

Woman in a camel trench coat over a soft knit sweater, black leggings, and red cowboy boots, strolling through a festive snowy street with holiday lights

18. For a warm, elegant winter look, go for a deep green wool coat over a red knit sweater and black leggings.

Tan cowboy boots add a rustic touch, while the color combination brings festive cheer.

This outfit is perfect for indoor gatherings or cozy evenings by the fireplace, embodying a classic holiday feel.

a woman wears a red sweater, black leggings, long green coat and brown cowboy boots

19. For a unique winter look, layer a cream-colored fringed poncho over a teal top and matching leggings.

Complete the outfit with white cowboy boots and a wide-brimmed hat to bring in that Western flair. This bohemian-inspired outfit is perfect for outdoor gatherings or scenic winter getaways.

A woman wears white cowboy boots, mint leggings with a cream poncho

20. Stay warm and stylish in an oversized, chunky-knit cream sweater with light gray textured leggings. Beige cowboy boots with a slight heel add a refined touch to this cozy look.

This outfit is perfect for holiday markets or cozying up by the fireplace, combining comfort with elegance.

A woman sits comfortably in a chunky knit cream sweater and leggings with brown and beige cowboy boots

21. Give off a chic urban vibe with an oversized gray sweater and black faux leather leggings.

White cowboy boots add a modern twist, bringing brightness to the darker tones of the outfit. This look is casual yet trendy, perfect for running errands or grabbing a coffee in the city.

A woman wears white cowboy boots with leather leggings, a sweater

22. Layer a classic camel coat over a white blouse and black leather leggings for a polished winter outfit.

White cowboy boots add a stylish Western touch, while a statement belt buckle adds a bit of personality.

This outfit is great for day-to-night wear, balancing sophistication with casual Western charm.

A woman wears white cowboy boots with leather leggings and white top and a trench coat

These winter-ready outfits with cowboy boots and leggings showcase the versatility of Western style, offering inspiration for every setting from city streets to rustic retreats.

Experiment with textures, colors, and accessories to make these looks your own, and embrace the charm of cowboy boots all winter long!

Ankle Cowboy Boots and Legging Outfits for Winter

Ankle cowboy boots bring a modern twist to traditional Western style, making them a versatile option for pairing with leggings.

These shorter boots are perfect for winter as they’re easy to wear, add a sleek silhouette, and can be styled with both casual and polished looks.

Here’s how to style ankle cowboy boots with leggings this winter.

1. For an understated yet chic look, pair black leggings with a matching black sweater and a long textured coat in a neutral brown.

Tan ankle cowboy boots add a warm contrast, while a beanie and gloves complete the outfit, adding both style and warmth. Perfect for casual city strolls.

A woman in black leggings and brown suede short cowboy boots, styled with a thick wool coat in a warm, neutral tone, accessorized with a knitted beanie and leather gloves

2. Opt for a laid-back look by combining black leggings with an oversized plaid coat.

Tan ankle cowboy boots bring a rustic touch, while a chunky scarf and leather gloves keep you warm. This outfit is ideal for outdoor winter activities where comfort meets style.

A woman in black leggings paired with brown suede short cowboy boots, wearing an oversized plaid coat, a thick knitted scarf, and leather gloves

3. Make a statement with green leggings and a camel-colored belted coat.

Black ankle cowboy boots and a wide-brimmed black hat add a bold Western flair, making this outfit perfect for festive winter markets or holiday events where you want to stand out.

Fashion-forward woman in a camel-colored wool coat, leggings in dark green, and sleek black cowboy boots

4. Pair plaid leggings with a gray long coat and a matching knit beanie for a cozy, classic winter vibe.

Tan ankle cowboy boots complete the outfit, adding a touch of Western style to an otherwise traditional winter look. Great for leisurely days in the park or casual outings.

Casual winter look with a woman in a gray wool coat, leggings in a plaid pattern, and tan cowboy boots

5. Achieve a polished Western-inspired look by pairing black leggings with a white turtleneck and a plaid long coat.

White ankle cowboy boots add a fresh, modern contrast. Add a white felt hat for extra style points, perfect for holiday gatherings or evening events.

A woman in short white cowboy boots styled with black leggings and a cream turtleneck under a plaid wool coat, with a matching beanie

6. Stay ultra-cozy with black leggings and a beige puffer jacket. Pair this with tan ankle cowboy boots and a woven scarf for a functional yet stylish winter look.

This outfit is perfect for snowy walks or casual outdoor activities, keeping you warm without sacrificing style.

Woman wearing a puffer jacket, knit hat, dark leggings, and beige cowboy boots, standing in a small snow-covered town square

7. For a warm, inviting look, try burgundy leggings paired with a chunky cable-knit sweater in a soft, neutral color.

Brown ankle cowboy boots ground the outfit, adding a Western touch. This cozy ensemble is ideal for forest walks or relaxed winter days.

A woman wears short brown cowboy boots, leggings and a chunky sweater

8. Create a casual, easygoing look with gray textured leggings and a black cardigan.

Tan ankle cowboy boots add a subtle Western element, making this outfit perfect for laid-back days in the park or grabbing coffee with friends.

A woman wears short brown cowboy boots, leggings, black jacket and black underneath shirt

9. For a vibrant look, pair black leggings with a mustard yellow cardigan. White ankle cowboy boots add brightness and a playful twist.

This outfit is great for outdoor events or casual gatherings, bringing warmth and cheer to the winter season.

A woman wears white ankle cowboy boots with leggings, white top and long yellow cardigan

10. For an edgier outfit, pair black leather leggings with a maroon turtleneck. White ankle cowboy boots add contrast, bringing a touch of Western charm to this sleek look.

This outfit is perfect for urban settings, offering style and a bit of attitude for winter.

A woman wears white cowboy boots, leather leggings and a dark red turtleneck

11. For a soft, neutral look, pair olive green leggings with a cream parka and white ankle cowboy boots. Add a beige scarf and a knit hat to stay warm and stylish.

This look is perfect for a quiet walk in the park on a snowy winter day, blending warmth with understated elegance.

A woman wears white cowboy boots, green leggings and a down jacket

12. Combine light gray leggings with a cozy, oversized pink cardigan for a soft and approachable look.

White ankle cowboy boots add a gentle Western touch, while a neutral scarf keeps you warm. Ideal for city outings or coffee shop hangs, this outfit is comfortable and effortlessly stylish.

A woman wears white cowboy boots with leggings and a pink coat

13. For a sleek city vibe, pair deep green leggings with a black turtleneck and a long black wool coat.

Brown ankle cowboy boots and a black hat bring a hint of Western flair to this bold, urban outfit. Great for winter walks downtown, this look is stylish and ready for the snow.

A woman wears brown cowboy boots, olive leggings and a coat

14. Burgundy leggings paired with a fluffy beige faux fur jacket create a cozy, eye-catching look.

Tan ankle cowboy boots add warmth, while a matching beanie and scarf keep you snug. This outfit is perfect for wintry hikes or holiday events, mixing comfort with a touch of glam.

A woman wears brown cowboy boots, burgundy leggings and a fur coat

15. Go bold with metallic silver leggings, a fitted black coat, and white ankle cowboy boots.

This look is edgy and unique, ideal for making a statement in the city. Perfect for those who like to mix classic Western style with a modern, futuristic twist.

A woman wears white cowboy boots with silver leather leggings and black trench coat

16. Pair black leggings with a white top and a camel trench coat for a polished winter look.

White ankle cowboy boots add a fresh contrast, making this outfit both sophisticated and versatile. This is a great choice for a stylish yet comfortable outfit that works for both day and evening.

A woman wears white cowboy boots with leather leggings , white top, and trench coat

17. For a cozy, rustic vibe, pair gray leggings with a rich burgundy cardigan.

Brown ankle cowboy boots add a warm, earthy touch, creating an outfit perfect for casual gatherings or outdoor fall-inspired photos. This look brings together comfort and rustic charm with ease.

a woman wears leggings, brown cowboy boots with a brown cardigan

Each of these outfit ideas combines the warmth and functionality of leggings with the unique style of ankle cowboy boots, creating looks that are both comfortable and winter-ready.

Black Cowboy Boots and Leggings Outfits for Winter

Black cowboy boots bring a sleek, edgy touch to winter outfits. When paired with leggings, they create a streamlined silhouette that’s easy to style and ideal for colder weather.

Here are some stylish ways to incorporate black cowboy boots into your winter wardrobe with leggings.

1. Pair burgundy leggings with a navy double-breasted coat and a matching scarf.

Black cowboy boots ground the look with a sophisticated touch, while the rich colors create a striking winter palette.

Perfect for city outings or festive events, this look is polished and effortlessly chic.

Chic winter outfit with a woman wearing a long navy blue coat, leggings in burgundy, and black cowboy boots

2. For a cozy and approachable look, combine black leggings with a cream winter coat and a patterned scarf.

Black cowboy boots add a rugged edge, making this outfit ideal for snowy hikes or relaxed days in nature.

Woman wearing a parka with a cozy scarf, black leggings, and black cowboy boots, standing along a snow-covered trail with frosty evergreens around

3. Go for a chic, all-black outfit by pairing black leggings with a fitted black turtleneck. Black cowboy boots keep the look streamlined, while the monochrome style adds sophistication.

This outfit is perfect for evening events or holiday gatherings, blending simplicity with elegance.

a woman wears a black sweater, black leggings, and black cowboy boots

4. Combine black leather leggings with a chunky cream turtleneck and a dark wool coat. The black cowboy boots add a cohesive look to this texture-rich outfit.

Ideal for winter walks or casual meetups, this outfit keeps you warm while maintaining a refined style.

Woman in a wool coat layered over a cream sweater with leather-look leggings and black cowboy boots, standing in a frosty winter forest

5. Add a Western twist with black leather leggings, a dark top, and a plaid shawl.

Black cowboy boots enhance the Western vibe, making this outfit perfect for outdoor winter events or casual weekends. The plaid brings warmth and character to the look.

a woman wears a plaid shawl, black leggings and black cowboy boots

6. Create a sophisticated winter look by pairing black leggings with a long burgundy coat.

Black cowboy boots add an edgy touch, balancing the elegance of the wine tones. This outfit works beautifully for snowy city streets or winter markets.

a woman wears a burgundy coat, black shirt, leggings and black cowboy boots

7. For a relaxed, cozy look, pair navy leggings with a white blouse and an oversized beige cardigan.

Black cowboy boots keep the look grounded, while the soft layers make it perfect for casual days. This outfit combines comfort with just the right amount of Western flair.

a woman wears navy leggings, black cowboy boots, a white blouse with a long cardigan

8. Contrast winter whites with black by pairing a chunky white sweater with black leggings and black cowboy boots.

This outfit is simple yet stylish, great for a casual stroll through snowy streets. The black boots give it a modern, slightly edgy look.

a woman wears a white sweater, black leggings and black cowboy boots

9. Go for an oversized beige sweater with black leather leggings for an effortlessly chic look.

Black cowboy boots add a sleek, edgy touch to the soft textures, creating an outfit that’s both comfortable and stylish. This is perfect for city outings or casual gatherings.

a woman wears a beige sweater, black leggings and black cowboy boots

10. Complete your winter look with a burgundy textured coat, gray leggings, and black cowboy boots.

This outfit is perfect for holiday gatherings or festive outings, combining cozy textures with a touch of Western charm.

A woman wears black cowboy boots, leggings and a long coat

11. Go for a modern, minimalist look with deep green leggings and a fitted gray turtleneck, topped with a long gray coat.

Black cowboy boots bring contrast and a subtle Western touch to the monochromatic outfit, making it a great choice for an urban setting where style and warmth are key.

a woman wears leggings, black cowboy boots and a grey trench coat

12. Pair dark navy leggings with a chunky navy cardigan and a matching tee. Add a belt for definition and complete the look with black cowboy boots.

The rich navy tones create a cozy, cohesive outfit that’s perfect for a laid-back day out while still looking polished.

a woman wears a navy cardigan, black cowboy boots and leather leggings

13. For a timeless look, style black leather leggings with an oversized white knit sweater.

Black cowboy boots ground the outfit with a hint of Western flair, making it versatile enough for both casual and slightly dressier occasions.

This outfit is ideal for winter city strolls or relaxed social gatherings.

a woman wears a white sweater, leather leggings and black cowboy boots

14. Embrace a structured look with black leather leggings, a black top, and a tan trench coat.

Black cowboy boots add a Western touch, bringing a bit of edge to the polished style. This outfit is perfect for days when you want to look put-together and stylish, with a hint of rugged charm.

a woman wears black cowboy boots, a black top, black leggings and a trench coat

Each of these black cowboy boots and leggings outfits combines cozy winter layers with sleek Western details, offering style and comfort for any winter occasion.