Skip to Content
From The Guest Room is reader-supported. When you buy through links on our site, we may earn an affiliate commission. Read more

10 Winter-Ready Outfits with Cowboy Boots and Leggings

10 Winter-Ready Outfits with Cowboy Boots and Leggings

Hey there, fashion lovers! As the snowflakes start to fall, it’s the perfect time to talk about keeping warm and looking cool.

We’ve put together some snuggly, stylish outfits with your favorite leggings and trusty cowboy boots that’ll make you love the chilly weather.

Get ready to mix, match, and make your winter wardrobe an enjoyable experience. Let’s get into it and keep things cozy yet fabulous!

Ankle Cowboy Boots with Leggings Outfits for Winter

When winter whispers, it’s time to pair those snug leggings with ankle boots for a warm and stylish look.

Embracing the chill doesn’t mean sacrificing fashion, and these outfit ideas serve as the perfect inspiration for your cold-weather wardrobe.

Idea #1:

Bundle up in a chunky knit sweater and black leggings, elevated by sleek black leather ankle boots.

A woman wears sweater and black cowboy boots

A touch of elegance is added with a simple pendant necklace and a matching leather handbag for a perfect coffee run ensemble.

Don’t forget to top it off with a cozy beanie, blending comfort with a hint of street style.

A woman wears sweater, black leggings and black cowboy boots

Idea #2:

Marrying the edge of a black leather jacket with the ease of leggings, this look is given a playful twist with tan ankle boots adorned with tassels.

It’s the perfect blend of tough and tender. Accessorize with a casual watch or a stack of bangles to bring some personality to the mix. A woman wears suede boots with leggings and red top

This has become one of my staples for days when I want to feel put together but still comfortable enough to tackle whatever the day throws at me.

Idea #3:

Stride out in confidence with shiny black leggings paired with suede ankle boots, a combination that screams urban chic.

Wrap yourself in a luxurious oversized fur coat, and accessorize with leather gloves and a classy tote bag.

A woman wears black ankle cowboy boots, leggings and cardigan and is holding a handbag

This outfit is my go-to for those frosty mornings that call for an extra layer of glam.

Layer Style with Leggings, Blazers, Trench Coats, and Beyond

Winter is all about layers, and there’s no better way to showcase your style than by adding some dimension to your leggings and boots combo.

Each layer is a new opportunity to play with textures, colors, and accessories, creating a unique look that’s all you.

Idea #1:

Opt for a classic, tailored look with a black pea coat over a red plaid shirt. The grey ankle boots add a subtle contrast, while the leggings act as a sleek base.

A woman wears leggings with beige ankle boots

Whether it’s office hours or after-work drinks, this power outfit has you covered.

Idea #2:

Make a statement with a vibrant teal coat, bringing a pop of color to winter days.

Pair with a simple white sweater, black leggings, and comfortable black ankle boots.

A woman wears ankle boots with trench coat, leggings and handbag

A wide-brimmed hat and a structured handbag are the perfect accessories to complete this bold, yet sophisticated, outfit.

Idea #3:

Embrace earthy tones with chocolate brown leggings and complementary knee-high suede boots.

An oversized chunky knit sweater in warm hues adds a cozy texture, perfect for a laid-back afternoon stroll.

A woman wears skinny pants, sweater, leather bag and cowboy boots

The ensemble is complete with a matching leather shoulder bag that says you’re ready for wherever the day may take you.

Idea #4:

Embrace a minimalist aesthetic with a draped grey tunic over black leggings, complemented by distressed ankle boots.

A woman wears grey dress, black leggings and boots

This ensemble is about effortless elegance, perfect for those days when you want to look put-together with minimal fuss.

Idea #5:

Navigate the cityscape with an edgy twist by layering a black leather jacket over a tailored blue shirt, topped with a black mini skirt.

The ensemble is anchored by black leggings that blend seamlessly into taupe ankle boots.

A woman wears legging with black skirt, jacket

This is a function and fashionable outfit, carrying you from the hustle of the workday to the buzz of a night out.

Don’t forget a spacious black leather tote to carry your essentials — because a woman on the go should never have to compromise on style or practicality.

Idea #6:

Channel a sleek silhouette with a navy belted coat with a fur collar, paired with black leggings and ankle boots.

A woman wears black cowboy boots with leggings

This look is all about streamlined shapes and is ideal for those who appreciate a bit of luxury in their everyday wear.

Idea #7:

Nothing says winter wonder like a bold red coat, a true statement piece over classic black leggings and sleek knee-high boots.

Accessorize with a black hat and gloves to keep warm while looking effortlessly elegant.

A woman wears black cowboy boots, red trench coat and leggings

This outfit is a holiday season favorite, and it’s perfect for those snowy days when you want to stand out against the winter white.

Wrap it up

To cap off, winter style doesn’t mean bulky layers that hide your flair.

It’s about smart pairings like leggings with cowboy boots and strategic layering for warmth and wow factor.

Keep it cozy, keep it chic, and let your boots leave a stylish footprint in the snow!