Eight Cute Winter Outfits with Cowboy Boots

Draw inspiration for your look this season with these cute winter outfits with cowboy boots. Whether you’re attending weddings and holiday parties or riding in the arena, browse our style recommendations on how to wear cowboy boots in the winter.

Cowboy boots are a versatile, well-loved classic for their function and flexibility. And now, Western footwear has never been more in fashion. In our opinion, winter outfits just aren’t complete without a pair of cowboy boots. We’ve pulled together our recommendations for eight cute winter outfits with cowboy boots so you can keep your boots on all season long. Let these ideas for winter cowgirl outfits inspire you to enjoy the season to the fullest!

1. Cowboy Boots and Skirts

Even in winter, outfits with cowboy boots and skirts can be cosy and cute. The skirt-and-boots combination is always a winner, and while any cowboy boot will work for this look, try boots with a long shaft that hits around mid-calf. Go for a skirt that’s fitted rather than loose, like a denim skirt or an A-line mini, and pair it with sheer tights to add warmth and keep your legs covered. Have fun with it — match plain leather boots with a bold colour or patterned skirt, or vibrant boots with a neutral bottom.

The best way to finish this look is with a long jacket. Find a layer longer than your skirt but above your boot top to highlight the combination. If the weather warrants, wear it open to show off the whole outfit!

2. Jeans Tucked into Cowboy Boots

Winter country outfits often feature cowboy boots with bootcut jeans worn untucked, but we love the look of tucked-in jeans. Try pairing women’s Western boots with tucked-in fitted leggings, jeggings or skinny jeans — the perfect combination for enjoying classic outings of the cold-weather season, like gazing at holiday lights or walking around a Christmas market.

Skinny jeans with a bit of stretch or leggings are the right choice for the tucked-in look, as they naturally shape to the leg and won’t add bulk in your boot. Go for a dark wash during this time of year, opting for navy or even black denim, and pair it with something sporty, like a performance zip fleece. A knit beanie (puff optional) will keep you warm and toasty.

3. Boots and High-Waisted Denim

Another top contender among winter cowboy boot outfits is the elegant, semi-retro combination of high-waisted jeans and cowboy boots. Stick with a tall cowboy boot and keep it simple and classic in your colours. High-waisted jeans can flatter your waist and often feature cute and unique touches like button-up closures that make them stand out. Tuck in a fitted mock or turtleneck and accessorise with a belt with a sterling silver or gold buckle, matching the colour on your jean buttons or pulling out an accent colour from your boots.

4. Cowgirl Boots and Ripped Jeans

Don’t lose your personal style when exploring how to wear cowboy boots in the winter. Embrace an alternative fashion trend with your cowboy boots outfit this winter by rocking heavily ripped jeans. Try distressed black jeans and match your cowboy boots to the leather on a bomber jacket. Or let your boots add a dramatic flair to the otherwise dark look with embellishments like studs or a spark of colour. Short or tall cowgirl boots will work here; check out our best-selling Darlin Western boots or Heritage R Toe Western boots to complete your outfit.

5. Ankle Booties and Rolled Jeans

Pair your favourite ankle booties with rolled-up jeans for this street-casual look. An oversized flannel or shirt-jacket keeps it relaxed. Or, bring along a quilted gilet and a scarf for the ultimate cosy vibes. Pair with a short ankle boot like our Darlin Western boots to complete the look.

6. Winter Dress with Cowboy Boots

When paired with layers in your winter cowgirl outfit, the right dress can be versatile and warm. Whether you’re going to a wedding or just dressing up for date night, you’ll love the look of a long maxi dress with cowboy boots. Go for a dress that has a small slit to reveal some of your boot, but layer and dress it up with a soft, faux-fur jacket or a simple, classic cardigan with an elegant boot.

7. Boots Untucked with Flared Jeans

This classic look is always in style. Pair your favourite wide-leg or flared denim with your go-to cowboy boots. Since you’ll mostly see the toe of your boot, show off a square or pointed-toe boot. Other must-have accessories are a leather belt and a Western-style blouse. Instead of the expected cowboy or cowgirl hat, try out a fleece headband for fashion-forward warmth.

8. Boots and Coats

Cowboy boots and oversized coats complement each other in an easy winter pairing. Whether you rock jeans, a dress, or a skirt, you can’t go wrong with throwing on your boots and a long coat or parka. Shop for wool, tweed, or down in timeless patterns like plaid or neutral colour pallets like grey, black, tan or cream that match anything. Find something you’ll be glad to bundle up with throughout the season — bonus points for memorable details like big buttons, zip pockets and dramatic collars.

Now that you have cute ideas for winter cowboy boot outfits, shop for the pieces you need to fill out the look by browsing the Ariat collections. Don’t miss new additions to our collection of women’s and men’s Western boots that make the perfect pieces for pairing.