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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

A laid-back winter vibe is easy to pull off with gray leggings, a chunky knit sweater, and a plaid longline coat layered over.

Pair it with classic brown cowboy boots to add that rustic charm while staying comfy.

Let your hair loose and skip the accessories for a relaxed day at the market or a casual brunch stroll.

A woman wears gray fleece-lined leggings with dark brown cowboy boots, a cable-knit pullover, and a long plaid coat

Looking to turn heads during holiday festivities?

Try burgundy leggings paired with white cowboy boots and a faux fur vest layered over a fitted gray top.

A white beret and soft curls add a playful Parisian twist that feels fun and festive for winter towns or Christmas village visits.

A woman wears burgundy leggings tucked into white cowboy boots, paired with a faux fur vest and a thermal long sleeve top

For foggy mornings and country drives, taupe leggings and a soft sweater layered under a puffer coat give just the right amount of warmth.

Tan cowboy boots and a neutral baseball cap keep it grounded and practical.

Throw on sunglasses for an effortlessly cool finish that works from sunrise to lunch stops.

A woman over 40 wears gray leggings and light brown cowboy boots, styled with a neutral sweater and padded jacket

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

How about mixing texture with attitude?

Pair faux leather leggings with a cream sweater featuring voluminous sleeves and layer on a chunky knit scarf.

Black cowboy boots and a sleek crossbody bag tie everything together for a street-style-ready look in snowy cityscapes.

A woman wears shiny leggings and black cowboy boots, styled with a puff sleeve sweater and oversized wool scarf

Planning an evening at a winter festival or light show?

Opt for dark leggings, a cozy fur jacket, and heeled embroidered cowboy boots for a blend of warmth and glam.

A low-cut top and minimal jewelry strike the right balance between cozy and flirty.

A woman wears leggings with bold western boots, a fitted long sleeve tee, and a fur-lined coat, standing in front of a winter carnival

A red chunky cardigan over a black fitted tank and leggings offers a bold yet relaxed winter combo.

Brown cowboy boots and a wide-brim felt hat pull the whole rustic look together.

Perfect for lakeside strolls or sipping cocoa outdoors during golden hour.

A curvy woman wears black leggings and cowboy boots, styled with a chunky red cardigan and winter hat

For those snow-covered trails or cabin escapes, go for an oversized rust-orange sweater with black leggings and fringe cowboy boots.

The earthy color palette and slouchy fit give it a relaxed and approachable feel.

Finish the look with a tan felt hat for that extra country charm.

A curvy woman wears black leggings and fringe-trimmed cowboy boots, layered with a rust-colored knit sweater and a wool hat

Embrace winter layering with chocolate brown leggings, a flannel shirt, and a cozy cream sherpa vest.

Classic tan cowboy boots keep things grounded while flattering the silhouette.

Keep accessories minimal and let your long waves and plaid do the talking.

A plus-size woman wears brown leggings and tan cowboy boots, a layered flannel shirt under a shearling vest

An olive green workout set paired with a long knit cardigan and worn-in cowboy boots brings together functionality and style for cold mornings near the woods.

Great for winter retreats or post-hike hangouts.

Keep the accessories simple and let the color combo do the work.

A woman wears olive green leggings with cowboy boots, a longline cardigan over a fitted top

For a soft and neutral winter palette, pair black leggings with a cream knit sweater and matching beanie.

Tall tan cowboy boots and a plaid scarf bring rustic flair that’s perfect for snow-covered trails or cozy winter cabins.

Keep the makeup natural and let the textures do the talking.

A woman wears black leggings with classic brown cowboy boots, a chunky beige sweater, and a plaid scarf

An oversized gray sweater with glossy black leggings creates a stylish contrast ideal for winter city strolls.

Wrap up in a chunky cream scarf and finish with black cowboy boots for a look that feels both warm and fashionable.

Great for outdoor shopping, coffee runs, or snowy date days.

A woman wears shiny leggings and black cowboy boots, styled with a puff sleeve sweater and oversized wool scarf

Channeling high-energy style, go for black faux leather leggings and a sequined top paired with embroidered cowboy boots.

This combo is bold, edgy, and perfect for concerts or dance nights in winter.

Keep accessories minimal and let the sparkle and boots steal the spotlight.

A plus size woman wears black leather leggings with a sequin top and embroidered cowboy boots

For a relaxed winter stroll in town, pair brown faux leather leggings with a white shirt and chunky knit cardigan.

Add tall tan cowboy boots and sunglasses for a polished yet laid-back vibe.

Perfect for sightseeing or casual holiday shopping.

A woman over 30 wears faux-leather leggings with tan tall cowboy boots and a white button-down shirt layered under a cozy cardigan

A brown babydoll tunic over black leggings gives a comfortable, breezy silhouette for outdoor winter events.

Style it with embroidered cowboy boots and layered jewelry to elevate the look.

This outfit feels easygoing while still feeling put together.

A plus-size woman over 40 wears a flowy tunic with leggings and embellished cowboy boots

Planning a day around town?

A tan cable-knit sweater with black leggings and camel cowboy boots creates a timeless winter outfit.

Add a small crossbody bag and loose curls for an effortlessly classic finish.

A curvy woman wears black leggings with an oversized camel knit sweater, paired with tall cowboy boots and a crossbody bag

Go festive with printed winter leggings and a cozy Fair Isle sweater for lounging by the fire or grabbing coffee at a mountain lodge.

Brown cowboy boots anchor the look and bring in a western touch.

Style your hair in loose waves and sip hot cocoa for the full vibe.

A woman wears winter-print leggings with chestnut cowboy boots, an oversized knit sweater, and mittens, sipping hot cocoa

An outdoorsy mood calls for olive leggings, a fitted knit tank, and a puffer vest for winter hikes.

Brown cowboy boots add a western twist to this otherwise active look.

Don’t forget sunglasses and a warm drink in hand for bonus comfort.

A woman wears olive green leggings tucked into rich brown cowboy boots, a waffle-knit henley top, and a quilted vest

On chilly rooftop nights or casual urban outings, go for gray leggings, a burgundy fleece jacket, and black cowboy boots.

Add a beanie and earmuffs to stay warm and playful.

It’s the kind of look that balances cozy comfort with a touch of personality.

A woman wears gray leggings tucked into black cowboy boots, a warm maroon fleece jacket, and earmuffs

Attending a holiday market or outdoor festival?

Pair navy leggings with a chunky lilac sweater layered under a puffer coat with faux fur trim.

Add embroidered cowboy boots, a crossbody bag, and a hot drink in hand to stay warm while soaking in the lights.

A woman over 40 wears navy leggings with distressed cowboy boots, a soft wool tunic, and a puffer jacket with faux fur trim

A mustard cable-knit sweater with chocolate leggings and classic tan cowboy boots makes a bold yet cozy outfit for cabin days or snowy strolls.

Style it with a faux fur hat to keep things fun and festive.

Red lipstick adds a playful pop that brightens the look.

A plus-size woman wears high-rise dark leggings with classic cowboy boots, a mustard cable-knit sweater, and a faux fur trapper hat

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

For a relaxed mountain retreat, burgundy leggings paired with a cream cowl-neck sweater and tan cowboy boots strike the perfect cozy balance.

Add a chunky knit headband for warmth without the bulk.

This outfit is ideal for sipping coffee on the porch or curling up by the fire.

A curvy woman wears burgundy leggings with tall tan cowboy boots, a loose-fitting cream cowl-neck sweater, and a fuzzy headband

A western twist on sporty winter wear, this look combines high-rise black leggings with a white crop top and cropped sherpa jacket.

Finish with dark cowboy boots and a wide-brim hat to bring full cowgirl energy.

Ideal for snow-covered fence-line photos or casual ranch outings.

A curvy woman wears thick black leggings with chocolate brown cowboy boots, a cropped ivory sherpa jacket, and a knit hat

If you’re visiting a winter village or strolling under the lights, try a knit oversized sweater over dark leggings and cowboy boots.

Top with a cozy beanie and a crossbody bag to keep things hands-free and practical.

It’s the kind of outfit that feels stylish yet snuggly all day.

A woman over 40 wears navy leggings with distressed cowboy boots, a soft wool tunic, and a puffer jacket with faux fur trim

Prefer polished and minimal?

Try black leggings with a gray knit sweater and a long tailored coat for a timeless winter outfit.

Black cowboy boots and a subtle smile finish the look perfectly for everyday city walks or weekend brunches.

A woman over 30 wears thermal black leggings with embroidered black cowboy boots, a soft gray turtleneck sweater, and a long wool 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.