14+ Ways to Style Cowboy Boots for Winter: Stay Cozy and Chic

Cowboy boots are a timeless fashion staple that can be worn all year round, including in the winter months.

Not only do cowboy boots add a touch of Western flair to any outfit, but they are also practical and versatile for colder temperatures.

In this article, we’ll explore how to wear cowboy boots in the winter, with tips and outfit ideas for different occasions.

Tecovas Waxed Canvas Trucker Jacket

14+ Outstanding Ways to Style Cowboy Boots for Winter

Here are some outfit ideas for wearing cowboy boots in the winter:

1. Oversized Blazer and Skinny Jeans, Dress or Skirt:

The oversized blazer and skinny jeans combination is a great way to create a casual yet edgy look that is perfect for the winter months.

To pull off this outfit, choose a blazer that is slightly larger than your usual size, but still fits well in the shoulders.

This will create a relaxed and stylish silhouette that complements the skinny jeans and cowboy boots.

As for footwear, cowboy boots are the perfect complement to this outfit. The sleek and stylish design of the boots adds a touch of ruggedness to the overall look, while also providing warmth and comfort.

Opt for a pair of boots with a slightly pointed toe to elongate your legs and create a flattering silhouette.

Pairing a blazer with a skirt is a timeless combination that can be dressed up or down depending on the occasion.

When choosing a skirt, opt for a style and length that flatters your body type and suits your personal style.

When choosing a blazer, look for a style that complements your skirt and your personal style.

A fitted blazer can create a classic and polished look, while an oversized blazer can add a touch of sophistication and edge. Experiment with different colors and textures to find a blazer that suits your taste.

Pairing a dress with a fur jacket and cowboy boots is a stylish and warm option for the winter season.

When selecting a dress, look for one that complements your body type and suits the occasion.

For a casual look, consider a flowy midi dress, while a fitted mini dress can create a more formal and polished look.

Pairing a dress with a fur jacket and cowboy boots is a stylish and warm option for the winter season.

When selecting a dress, look for one that complements your body type and suits the occasion. For a casual look, consider a flowy midi dress, while a fitted mini dress can create a more formal and polished look.

When it comes to choosing a fur jacket, opt for a style that complements your dress and personal style.

A classic faux fur jacket can add a touch of glamour to any outfit, while a more rugged shearling jacket can add an edgy and cozy touch.

Choose a jacket in a neutral color such as black, brown, or beige to make it easy to pair with your dress and boots.

To complete the outfit, choose a pair of cowboy boots that match the color of your dress or fur jacket.

Pointed-toe boots can elongate your legs and create a flattering silhouette, while ankle boots can add a modern touch to the outfit.

Consider wearing tights or leggings underneath your dress for added warmth.

2. Boot Cut Jeans and Denim Jacket:

Denim Trucker Jacket | Click image for more info on Tecovas

Opt for a pair of light wash boot cut jeans and pair it with a denim jacket.

Wear a simple white t-shirt underneath and complete the look with a brown belt and a pair of brown cowboy boots. This outfit is perfect for a casual night out with friends.

Denim Trucker Jacket | Click image for more info on Tecovas

3. Suede Fringe Jacket, Jeans, and Simple T-Shirt:

Start with a pair of skinny or straight leg jeans in a dark wash. Add a simple, solid-colored t-shirt in a complementary color, such as white or gray.

Layer a suede fringe jacket over the top of the t-shirt. Complete the look with a pair of cowboy boots in a neutral shade, such as brown or tan.

The suede fringe jacket adds a fun and trendy touch to the outfit, while also providing extra warmth during the winter months.

The jeans and t-shirt keep the outfit casual and comfortable, making it perfect for running errands, going to lunch with friends, or even a casual date night.

Suede Fringe Jacket | Click image for more info on Tecovas

When choosing a suede fringe jacket, look for one in a neutral color like brown or black, which will pair well with many different colors and styles of jeans.

The jacket should fit well and not be too bulky, as you want it to hang nicely when worn open. You can also accessorize with a statement necklace or earrings to add a bit of glam to the outfit.

Overall, this is a versatile and stylish outfit that can be dressed up or down depending on the occasion, and is perfect for showcasing your favorite pair of cowboy boots in the winter.

Suede Fringe Jacket | Click image for more info on Tecovas

4. Trucker jacket, T-shirt (or shirt) and Jeans

A trucker jacket paired with a t-shirt or shirt and jeans is a classic look that can be easily elevated with the addition of cowboy boots.

For a more casual vibe, opt for a simple t-shirt and bootcut jeans.

Waxed Canvas Trucker Jacket | Click image for more info on Tecovas

If you want a dressier outfit, go for a button-up shirt and dark wash jeans.

Overnight Trucker Jacket | Click image for more info on Tecovas

This look is versatile and can be worn in a variety of settings, from running errands to a night out with friends.

Just make sure to choose a trucker jacket that fits well and doesn’t overwhelm your frame.

5. Sweater Dress and Tights:

For women, pair your cowboy boots with a cozy sweater dress and opaque tights.  Add a scarf and hat for added warmth, and you have a comfortable and stylish outfit that is perfect for winter.

6. Plaid Shirt and Vest:

For men, pair your cowboy boots with a plaid shirt and vest. And you have a rugged and stylish outfit that is perfect for outdoor winter activities.

Tecovas Canvas Vest | Click image for more info on Tecovas

Lightweight Puffer Vest | Click image for more info on Tecovas

7. Fur Vest and Skinny Jeans:

For women, pair your cowboy boots with a fur vest and skinny jeans. Add a chunky scarf and hat for added warmth, and you have a chic and trendy outfit that is perfect for a night out.

8. Straight Jeans and Flannel Shirt:

Choose a pair of dark wash straight jeans and pair it with a classic red and black flannel shirt.

Tuck in the shirt and complete the look with a brown belt and a pair of brown cowboy boots. This outfit is perfect for a casual winter day out.

Flannel Overshirt | Click image for more info on Tecovas

9. Denim Jacket and Leggings:

For a casual and comfortable look, pair your cowboy boots with a denim jacket and leggings.

Add a beanie and scarf for added warmth, and you have an easy and stylish outfit for running errands or meeting friends for coffee.

10. Corduroy Pants and Sweater:

Pair your cowboy boots with corduroy pants and a cozy sweater. Add a scarf and gloves for added warmth, and you have a comfortable and stylish outfit that is perfect for any casual winter occasion.

11. Flannel Overshirt, Jeans, and T-shirt:

Choose a pair of straight or boot-cut jeans and pair it with a T-shirt. Layer a flannel overshirt on top of the t-shirt and leave it unbuttoned.

Complete the look with a brown belt and a pair of brown cowboy boots.

This outfit is perfect for a casual day out, running errands or meeting friends.

The flannel overshirt adds warmth and style to the outfit, while the jeans and t-shirt keep it simple and comfortable.

You can also swap out the flannel shirt for a denim or corduroy jacket to switch up the look.

Flannel Overshirt | Click image for more info on Tecovas

12. Faux Fur Coat and Midi Skirt:

For women, pair your cowboy boots with a faux fur coat and midi skirt. Add a turtleneck and gloves for added warmth, and you have a glamorous and chic outfit that is perfect for a winter date night.

13. Leather Jacket and Jeans:

For a classic and edgy look, pair your cowboy boots with a leather jacket and straight or bootcut jeans. And you have a timeless and stylish outfit that is perfect for a night out.

Goat Suede Overshirt | Click image for more info on Tecovas

14. Puffer Jacket and Skinny Jeans:

For a sporty and functional look, pair your cowboy boots with a puffer jacket and skinny jeans.

How to Choose Cowboy Boots for Winter

Let’s discuss how to choose the right cowboy boots for winter. Here are a few things to consider:

• Material:

Look for cowboy boots made from durable materials like leather or suede, which are naturally water-resistant and provide insulation to keep your feet warm in cold weather.

The Dillon Cowboy Boots | Click image for more info on Tecovas

• Sole:

If you often walk outside, look for boots with rubber soles, which will provide good traction on slippery surfaces.

Avoid leather soles, which can be slippery and dangerous in icy conditions.

• Height:

Consider the height of the boot shaft.

A higher shaft will provide more coverage and warmth for your ankles and lower legs, while a shorter shaft may be more comfortable and easier to walk in.

• Fit:

Make sure your cowboy boots fit properly. They should feel snug around the top of the feet, but not so tight that they’re uncomfortable.

You should also have enough room to wear thick socks for extra warmth.

Read more: Is it OK To Wear Cowboy Boots in The Snow?

• Style:

Choose a style that you like and that fits your personal style.

Firstly, cowboy boots come in a range of colors, from traditional brown and black to bolder shades like red and turquoise.

Consider which colors will work well with your winter wardrobe, and choose a pair that complements your style.

The Wyatt Cowboy Boots | Click image for more info on Tecovas

Secondly, there are many different designs of cowboy boots, including classic styles with stitching and embroidery, as well as more modern designs with unique embellishments or hardware.

Think about which design elements you prefer, and choose a pair that reflects your personal style.

Lastly, Cowboy boots also come in different toe shapes, from traditional pointed toes to more rounded or square shapes.

Consider which toe shape looks best with your foot shape and personal style.

Example:

1. Classic brown leather boots with traditional stitching and pointed toes. These versatile boots look great with jeans or leggings and can be dressed up or down.

The Jamie Cowgirl Boots | Click image for more info on Tecovas

2. Brown suede boots with a shorter shaft and pointed toe. These boots are stylish and comfortable, and the brown suede provides a nice contrast to lighter winter clothing.

3. Embellished boots with fringe, studs, or other decorative elements. These boots make a statement and are perfect for those who like to stand out from the crowd.

Don’t forget the socks

Wearing the right socks with cowboy boots in the winter can make a big difference in keeping your feet warm and comfortable.

Here are some tips:

• Wool socks:

Look for socks made from natural materials like wool, which can insulate your feet even when wet.

Merino wool is a great choice because it’s soft and warm, but also breathable.

• Thick socks:

Choose socks that are thick enough to provide cushioning and insulation, but not so thick that they make your boots feel tight.

• Over-the-calf socks:

Opt for socks that are tall enough to cover your calves and keep them warm, especially if you’ll be wearing shorter boots.

• Moisture-wicking socks:

Look for socks with moisture-wicking properties, which will help keep your feet dry and prevent blisters.

• Patterned socks:

Don’t be afraid to have some fun with your socks! Patterned socks can add a pop of color and personality to your outfit, while still being practical and comfortable.

Last words

In conclusion, cowboy boots are a versatile and stylish footwear option that can be worn in the winter with a variety of different outfits.

From casual looks with jeans and flannel shirts, to dressier outfits with dresses and blazers, there are endless ways to incorporate cowboy boots into your winter wardrobe.

When choosing cowboy boots for winter, opt for styles that are made from durable materials and have a non-slip sole for added safety on icy or wet surfaces.

It’s also important to choose boots that fit well and provide ample warmth, whether you opt for a classic design or a more modern style.

With the right styling and accessories, cowboy boots can be the perfect finishing touch to your winter outfits, providing both warmth and style.

So don’t be afraid to experiment with different looks and find the perfect pair of cowboy boots to suit your personal style and winter needs.

Jay Gatz

Howdy y’all, and welcome to From The Guest Room, your ultimate guide to all things Western! I’m Jay Gatz, a lifelong cowboy boot enthusiast with over 5 years of experience in the Western style world. I’m excited to share my knowledge with you and help you discover the perfect cowboy boots and western gear to elevate your style. Let’s explore the rich history and timeless appeal of Western fashion together!