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30+ Winter-Ready Outfits with Cowboy Boots and Leggings

By: Author Grace

Posted on  - Last updated:

30+ 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.

When the snow starts falling, pair black leggings with brown cowboy boots for a sleek, weather-friendly combo that still shows off your style.

A chunky cream turtleneck keeps things warm and layered under a long camel coat for added polish.

Great for winter strolls, casual meetups, or coffee runs in the city.

A woman wears black leggings, brown cowboy boots, and an oversized cream turtleneck sweater, layered with a long camel coat

For winter days at a snowy lodge or holiday trip to the mountains, try pairing black leggings with a Fair Isle sweater layered over a collared shirt.

The fitted base keeps it sleek while the knit adds that cheerful seasonal feel.

Round out the look with classic brown cowboy boots for a rustic, ready-for-anything finish.

A woman wears a red Fair Isle sweater layered over a chambray shirt, black leggings, and brown cowboy boots

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

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

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

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

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

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

Achieve an effortlessly stylish look by pairing a neutral-toned long coat with a brown sweater, 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

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

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

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

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

Opt for a laid-back look by combining black leggings with a black top and 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.

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

Pair plaid leggings with a matching top, 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. This outfit is 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

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

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

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

Create a casual, easygoing look with gray textured leggings, a black top and 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

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

For a soft, neutral look, pair olive green leggings with a cream parka, matching sweater 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

Combine light gray leggings with a simple top and 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

Burgundy leggings paired with a sweater and 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

Go bold with metallic silver leggings, a fitted black coat, a neutral top 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

Pair black leggings with a black turtleneck layered under 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

Pair burgundy leggings with a navy double-breasted coat, a simple top 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

For a cozy and approachable look, combine black leggings with a cream or beige 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

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

Complete your winter look with a burgundy textured coat, a black sweater, gray jeans, 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

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

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.