How To Transition Your Cowboy Boots To Work With All Of Your Winter Looks

Each season seems to bring along an unexpected shoe trend, from summer platforms to fall mules. It has left many of us wondering which shoe will take the reins this winter. While not a traditional winter shoe, western boots have proven to be both an influencer and celebrity favorite for the season. They even dominated the runways for some of the most notable heritage brands, such as Chanel, in their fall-winter 2022/23 show. When speaking to Refinery29 about must-have wardrobe pieces for fall, fashion director for Shopbop, Caroline Maguire emphasized the versatility of western boots for the season by saying, "play up all the colors, leather, and suede variations, and explore which shaft height works best for you."

The buzz is still surrounding cowboy boots this winter season. From Kendall Jenner rocking a unique, fuzzy pair to Dua Lipa posing in her black cowboy boots on Instagram, we have seen the look styled in a variety of ways. If you're looking to transition your favorite cowboy boots into winter, look no further! We have curated six ways to step into a winter wonderland while still rocking the cowboy boot trend.

Contrast with a blazer

When you play with contrast in an outfit, it makes it more visually appealing. We often see this done by pairing together casual pieces with classy pieces. This winter, a great way to style your cowboy boots is by adding a blazer to your usual look. The addition of a blazer will give you an extra layer to keep warm while also adding a reason to make the cowboy boots pop. Instagram fashion influencer Chantal Alicia shows us how adding a pair of suede cowboy boots to a winter blazer look brings the outfit full circle.

Classic sweater and jeans look

You can never go wrong with a basic jeans and sweater look during the winter. The look plays off the coziness of the season and, with the right accessories, can turn into a fashion-forward outfit. Jessica Blackman posts daily outfit inspiration to her Instagram account, where she recently shared her take on a modern cowgirl look. To create the look, Blackman paired a classic black sweater and jeans look with a leather jacket, bucket hat, and black cowboy boots to take the look from good to great.

Sweater dress and cowboy boots

When searching for how to rock the winter sweater dress, one of the most common questions that arise is, "what shoes should I wear?" Sneakers are great for a basic, everyday look but if you are looking to bring your western boots into winter, wearing them with a sweater dress is a great way to do it. When sharing ways to style your favorite sweater dress this winter on YouTube, The Simple Mindset states that she loves pairing it with a pair of cowboy boots and a chain belt.

Denim on denim on denim

Denim-on-denim looks are nothing new to the fashion scene. With the resurgence of Y2K era fashion, it is only natural that the look made mainstream by Brittany Spears and Justin Timberlake would have its time in the spotlight. Nothing pairs better with a winter denim look than the traditional cowboy boot. Take lead from Instagram blogger @goar.a, who styled white denim skinnies with a denim button-up and a denim jacket over top. She rounded out the look with black cowboy boots.

Slip dress and jacket

The slip dress is not leaving the fashion scene just because it is cold outside. There are plenty of ways to style a slip dress in winter, with both layerings over and under the dress. Our personal favorite way is to style a unique jacket over the slip, adding fun accessories to compliment the look. Self-proclaimed fashion enthusiast Sevenagh McLaughlin shared an Instagram photo showing exactly how the look can work. She paired a purple slip dress with a zebra print jacket and white cowboy boots proving the look to be both warm and stylish.

With a longline coat

Longline coats are a winter staple. Luckily, we already often see the longline coat look styled with knee-high boots. This winter, a western spin will be put on the traditional knee-high boots and long coat look. When styling this look, ensure that you wear a shorter dress or skirt underneath the longline coat, so the top of your boots can still be seen. Fashion blogger and UGC creator Pavli Ostrolucka rocks the look on her Instagram with a brown longline coat over a turtleneck and mini skirt, with knee-high cowboy boots being the focus.