7 Different Outfits To Wear With Cowboy Boots For Men

How can you wear Cowboy boots without appearing like a rodeo clown can be your biggest concern if you are a newcomer to the scene.

how to wear cowboy boots

Fret not, because you’ve landed in the right space where we decode the art of rocking cowboy boots with a contemporary flair.

While the classic pairing with ordinary boot-cut jeans is a safe bet, we believe there are more imaginative and stylish ways to integrate cowboy boots into your wardrobe. Given the extensive variety available, this presents a chance to infuse a distinctive and unique element into your personal style.

What Wearing Cowboy Boots say about a man

Wearing cowboy boots can reveal quite a bit about a man’s style and personality. For starters, it might indicate a deep connection to tradition, reflecting a respect for the rugged, outdoor heritage associated with the cowboy lifestyle. There’s something inherently individualistic about cowboy boots – a choice that breaks away from the mainstream fashion norms, suggesting a desire to express one’s unique identity.

Beyond just fashion, the decision to wear cowboy boots can speak volumes about a man’s confidence. These boots are often a statement piece, standing out with their bold style and intricate detailing. Opting for such attention-grabbing footwear suggests a level of self-assuredness and a willingness to embrace distinctive fashion choices.

Practically speaking, cowboy boots are known for their comfort and durability, appealing to those who value footwear that can withstand various conditions. This practicality aligns with a down-to-earth attitude, emphasizing functionality without sacrificing style.

Also read: A Comprehensive Guide to Cowboy Boots in 2023

Moreover, the love for country or Western culture is embedded in the essence of cowboy boots. Wearing them could signify an appreciation for aspects of this lifestyle, whether it’s country music, rodeos, or a connection to the great outdoors.

In the realm of fashion, the versatility of cowboy boots is often underestimated. Traditional or modern, these boots can effortlessly transition from casual to semi-formal settings, revealing a man’s appreciation for adaptable wardrobe choices.

Delving into the details, the craftsmanship of cowboy boots showcases a keen eye for detail. The intricate designs and stitching tell a story of someone who appreciates well-crafted, quality items.

Ultimately, the decision to wear cowboy boots is a personal one, shaped by a combination of style preferences, cultural influences, and practical considerations. It’s a unique expression that goes beyond footwear, offering a glimpse into the diverse facets of a man’s character and tastes.

Here Are 6 Outfits You Could Wear Cowboy Boots With


Cowboy boots often come with intricate stitching on the boot shaft that tends to be hidden beneath your pants. To highlight the unique design of your boots, a cool trick is to cuff your jeans. This simple move not only draws attention to the decorative details of your boots but also lets them shine even when you’re seated.

You don’t need any special kind of jeans for this style; just opt for a comfy pair of relaxed-fit, straight-leg jeans. Choose a slightly longer length than your usual size to ensure you have enough denim to create a stylish cuff.

To complete the look, pair your cuffed jeans and cowboy boots with a casual t-shirt or layered button-down shirts. It’s as easy as that to showcase your boots in a laid-back, stylish way.


Generally, jeans have stitching at the bottom, which we call the hem. Well, raw hem jeans skip that whole stitching thing and go for an unfinished look, letting the ends get all frayed. It’s a pretty hot trend these days, and it’s not just for the cowboy boot lovers out there. You can rock raw hem jeans with anything – sneakers, Birkenstocks, and, of course, cowboy boots. They really shine when they’re a bit on the shorter side, especially when you team them up with cowboy boots. Trust me, it’s a killer combo. Similar to cuffed jeans, the shorter, raw hem lets more of the boot shaft peek out when you’re sitting.

Any pair of relaxed-fit, straight-leg jeans will do the trick, but raw hems tend to pop more on lighter washes. Now, here’s the tricky part – you won’t find these babies just hanging on the store racks. Your best move is to grab a pair of jeans a tad longer than your usual and snip the ends to your liking. Some Levi’s stores might even do the cutting for you for a small fee.


White denim paired with brown or tan cowboy boots has a certain timeless charm. To effortlessly extend the life of your white jeans into the fall, consider combining them with other earthy tones or vintage oranges and yellows. Whether you prefer a raw hem or the classic look, maintaining a relaxed fit with no taper on the legs is key. Embrace the simplicity and versatility of this style to keep your wardrobe effortlessly chic.


Guess what? You’ve got more choices than just throwing on a pair of jeans to rock with your boots. Once you dive into various trouser styles, that’s when the fun and creativity kick in. A cool starting point is snagging a pair of vintage trousers that are laid-back around the hip and thigh but bring some flair as they flow down the leg. We’re not talking full-on bell bottoms here, just something with a bit more rise at the waist and a stylish touch of flare. You might need to hit up those vintage stores to track down the perfect pair, but trust me, they’re waiting out there for you.


When you think of pleated trousers, the first image that might pop into your head is those boxy suits from the ’90s or the khaki pants from high school. Well, guess what? Pleats are making a comeback, and they’re here to stay. And get this – you can totally rock pleated trousers with cowboy boots. The trick is to make sure they’re tailored just right, with no break in the leg. Aim for a sleek, clean line from waist to toe, and you’re good to go.


Forget what you’ve heard – you don’t need a Dallas tycoon’s bank account or Lyndon B. Johnson’s political swagger to rock cowboy boots with a suit. The real power move? Slipping into a sharp snip-toe boot that screams confidence. Look no further than the style game of country singer-songwriter Charley Crockett, who’s earned major street cred for his killer vintage wardrobe.

And guess what? You don’t have to shell out for a bespoke nudie suit to nail this look. Just grab a classic-cut suit (ditch the slim-fit pants) and make sure those trousers are tailored to perfection – a straight leg that grazes the top of your boots with no awkward breaks. That’s how you own the cowboy-boot-and-suit combo like a pro.


Wearing a cowboy boot with a full shaft isn’t always the most convenient, especially during the scorching summer heat. Some crafty bootmakers, such as Heritage Boots in Austin, have come up with a solution by crafting hybrid cowboy boots. These boots are ankle-high, reminiscent of a Chelsea boot, but they still boast a western heel and the classic stitching you’d expect from a traditional cowboy boot. It’s like hitting the sweet spot, especially if your closet is filled with slim-fitting denim.

How to wear cowboy boots without looking country

Cowboy boots embody the essence of Western style, having graced the feet of cowboys for centuries in a myriad of shapes, sizes, and colors. While some folks lean towards classic brown or black leather, others spice things up with vibrant hues.

These iconic boots aren’t limited to just men; there’s a fantastic array of styles for women too. If you’re on the lookout for a chic addition to your wardrobe, explore our selection of men’s and women’s cowboy boots today!

The cowboy boot isn’t just an emblem of American fashion; it’s also a fantastic way to elevate a casual ensemble. Those tall, wide-calf boots effortlessly infuse a touch of Western charm into your look, seamlessly complementing anything from jeans to dresses.

Yet, if you’re not accustomed to rocking cowboy boots, figuring out how to integrate them into your style without looking like you just stepped off a ranch can be a bit challenging. Here are some tips on how to stylishly wear cowboy boots after 50, ensuring this American classic becomes a staple in your day-to-day wardrobe.

Pair with Modern Pieces

Combine your cowboy boots with contemporary and on-trend clothing. Opt for sleek jeans, a stylish blouse or shirt, or even a chic dress to balance out the rustic feel of the boots.

Choose Neutral Colors

Pick cowboy boots in neutral tones like black, brown, or gray. These colors tend to have a more versatile and city-friendly appeal, making it easier to integrate them into a modern wardrobe.

Avoid Overly Western Accessories

While it’s fine to embrace a few Western-inspired details, avoid overdoing it with accessories like large belt buckles or cowboy hats. Stick to minimalistic and modern accessories for a more urban look.

Experiment with Different Styles

Cowboy boots come in various styles, including ankle boots or those with a lower heel. Opting for a more subtle version can help you achieve a contemporary appearance without sacrificing the essence of the cowboy boot.

Mix with Contemporary Fabrics

Incorporate modern fabrics like denim, leather, or even silk into your outfit. This contrast between traditional cowboy boots and contemporary materials can create an interesting and stylish ensemble.

Focus on Fit

Ensure that your cowboy boots fit well and complement your overall silhouette. This attention to fit can make the boots feel like a natural extension of your style rather than an out-of-place accessory.

Experiment with Different Outfits

Try out various outfits to discover what works best for you. Whether it’s a casual jeans-and-tee combo or a more polished dress, finding the right balance will help you wear cowboy boots with a modern flair.

Remember, the key is to mix and match, finding a balance that aligns with your personal style while incorporating the unique charm of cowboy boots into your urban wardrobe.

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