10+ Basic Outfit Ideas To Style Cowboy Boots for Men and Women

How to Wear Cowboy Boots for Men

This guide covers a range of styles, from classic rugged jeans to refined dress pants and suits. Its aim is to provide men with easy-to-follow, stylish outfit ideas that enhance the unique charm of cowboy boots.

Whether you’re going for a relaxed look or dressing up for a formal event, we offer versatile suggestions that go beyond the basics, ensuring that cowboy boots can be a stylish and functional part of any man’s wardrobe.

Jeans – Bootcut Jeans, Straight-leg Jeans and Cowboy-cut Jeans

“Hey, any of us know that jeans are the best accessory to wear with cowboy boots, do you know anything else?”

Yes, jeans are the best pants to wear with cowboy boots, but do you know what types of jeans to wear with cowboy boots aside from bootcut jeans?

I’ll let you know! And explain why you should choose them.

1. Bootcut Jeans

Jeans worn with cowboy boots are definitely the best combination life has bestowed on cowboy boots fans.

One of the jeans that is the best match with cowboy boots ever is the bootcut jeans. You can’t go wrong wearing bootcut jeans with cowboy boots.

The first thing is that bootcut jeans have enough room at the bottom for you to tuck the cowboy boot’s shaft inside.

In addition, bootcut jeans have a wide bottom and narrower upwards, which will not cause the V-shape of the collar cowboy boots to print on the surface of the jeans.

From the knee, the bootcut jeans hug the wearer’s body (hips, buttocks, thighs), creating a classic liberal look! And that’s exactly what you look for in cowboy boots.

2. Straight-leg Jeans

These jeans are characterized by a consistent leg width from the hip down to the ankle, creating a ‘straight’ silhouette.

Men’s Everyday Standard Jeans | Image copyright Tecovas Boot Company | #CommissionEarned

Unlike skinny jeans or flared styles, straight-leg jeans do not taper or expand towards the bottom. This design makes them a favorable choice for many body types.

When paired with cowboy boots, straight-leg jeans offer a distinct style. The jeans fit nicely over the boots’ shaft, so you can see part of the boots.

This combination is great for those who like a simpler look where the boots go well with the outfit without taking it over. It’s a nice way to show off cowboy boots in a more simple yet elegant way.

This combo is different from the typical cowboy look; it’s more elegant and refined. It’s for the guy who knows his style but also likes things classy and understated.

Now, here’s an important thing to remember when you’re wearing straight-leg jeans with cowboy boots: ensure the jeans have enough width at the bottom.

Why does this matter? Because you’ll want to comfortably slip the boots’ shaft underneath your jeans.

If the jeans are too narrow at the bottom, it won’t work well. They might bunch up strangely over your boots or not fit over them at all.

So, go for straight-leg jeans with a bit more room at the bottom. This way, you can easily tuck the boots’ shaft in, achieving a clean, sleek look.

3. Cowboy cut Jeans

What did I mention earlier? Along with cowboy boots, there are innovative accessories that can elevate your look, one of which is cowboy-cut jeans. These are modern jeans specifically designed for those who love to wear cowboy boots.

At first glance, cowboy-cut jeans may seem similar to bootcut jeans, but it’s important not to mix them up. The key difference lies in the size of the bottom hem.

Cowboy-cut jeans have a slightly slimmer bottom compared to bootcut jeans, but they’re still wide enough to snugly fit the shaft of your cowboy boots.

Image copyright Chisos Boot Company | #CommissionEarned | Chisos Cowboy Boots

So, what’s the appeal of cowboy-cut jeans? They offer a youthful, free-spirited, yet classic aesthetic. This style bridges the gap between traditional cowboy attire and contemporary fashion, making it a perfect choice for the modern wardrobe.

And if you think cowboy boots are not quite the trend among younger folks, think again. Pairing cowboy boots with cowboy-cut jeans is an excellent way to demonstrate how this timeless footwear stays stylish and on point even today.

It’s all about how you wear them — blending the classic charm of cowboy boots with the fresh, liberal vibe of cowboy-cut jeans can create a unique and appealing look.

4. Types of Jeans Fit Your Body Shape

No need to be rigid, the most important thing is to find the right jeans for your body and cowboy boots that fit them! Want some examples?

If you have a skinny body, you will need slim-fit jeans (slim-fit bootcut, slim-fit cowboy cut,…) to flatter your body. Because they hug your butt, thighs and hips fairly.

Believe me, you’ll look incredibly handsome and stylish in this outfit.

But what if you are overweight? Then the regular fit or relaxed fit will be a great choice, in terms of comfort and appearance.

Be flexible! Money and choice are yours!

Khaki Pants

Khaki pants are a must-have in your wardrobe, and they’ll definitely give you that authentic cowboy vibe, catching the attention of those around you!

Even though khaki jeans are in the jeans family, they offer a completely different style compared to normal jeans, especially when paired with cowboy boots.

If you want a rugged and worn-in look, then khaki jeans paired with cowboy boots are your go-to choice.

Image copyright Tecovas Boot Company | #CommissionEarned | Click the image for more info

There’s something special about pairing khaki pants with cowboy boots.

The dusty, rugged texture of khaki fabric brings an element of wild, masculine charm to your overall look. It’s a style that says a lot about the wearer’s strength and gentlemanly character.

So, why not give this style a try? Pairing khaki jeans with your favorite cowboy boots can change your look, giving you that rugged sophistication that’s hard to miss.

It’s a fashion statement that effortlessly blends the wild spirit of the cowboy with a polished, mature vibe. Give it a shot and discover how it enhances your cowboy ensemble!

Dress Pants

Gone are the days when cowboy boots were only linked to dusty ranches and sun-soaked fields.

Don’t be surprised if you see someone going to their office wearing cowboy boots with dress pants. This pairing has become a fashionable and refined option in modern fashion.

Today’s cowboy boots have expanded well beyond their traditional origins. They now come in various styles and are made from different materials, serving various purposes beyond ranch work.

Image copyright Tecovas Boot Company | #CommissionEarned | Click the image for more info

This transformation has turned them into a versatile option for different occasions, even in professional settings.

Just think about combining a stylish pair of lizard cowboy boots with well-tailored dress pants. You will get a classy and refined outfit for your workplace.

The Nolan from Tecovas | Image copyright Tecovas Boot Company | #CommissionEarned

It’s a look that breaks the mold, blending the rugged charm of cowboy boots with the polished finesse of formal attire. Why not give it a try?

It’s a perfect way to make a bold fashion statement that respects both tradition and modernity.

The Nolan from Tecovas | Image copyright Tecovas Boot Company | #CommissionEarned

Suits

Up to now, cowboy boots have changed a lot. They now come in polished finishes and luxurious exotic leathers. This means it is possible to pair cowboy boots with formal attire.

Modern cowboy boots with these fancy finishes and materials go well with a classic suit. They make your formal outfit look nice and unique.

Therefore, where you need to dress up for formal events such as business meetings, weddings, or fancy parties, consider wearing cowboy boots made from exotic materials (caiman, ostrich, or lizard leather) with polished finishes. These boots will elevate your outfit, giving you a classy and stylish look.

Image copyright Tecovas Boot Company | #CommissionEarned | The Marshall Boots

In the past, cowboy boots were mostly worn with casual or rugged clothes. But now, they can work for both Western charm and formal style.

If you want to make a strong fashion statement at your next fancy event, think about wearing your suit with a pair of high-quality, polished cowboy boots.

Jackets – Leather or Denim

Wearing a jacket with cowboy boots is a style must. When it comes to selecting the perfect jacket to complement your boots, leather and denim are your go-to choices.

Image copyright Tecovas Boot Company | #CommissionEarned | Tecovas Outerwear

These materials not only make you look more like a cowboy but also add a touch of rugged style to your whole appearance.

When picking a leather jacket, you should avoid overly shiny ones. Instead, go for jackets in distressed, tan, or brown colors.

These colors give you an authentic, worn-in look that goes well with cowboy boots. They also go with lots of different boot styles and colors.

Denim jackets are another excellent choice, especially if you want a matching outfit. You can match the color of your denim jacket with your jeans for a stylish, coordinated look.

This classic combination gives off a cool Western vibe that never goes out of style.

And remember, if you’re headed to a Rodeo, your jacket is an essential part of your attire. Leaving it behind means you’re missing a chance to show off your complete cowboy look.

A jacket not only adds to the aesthetic but also provides practicality, keeping you comfortable and in style whether you’re watching or taking part in the event.

T-shirts or Shirts

When you’re matching tops with jeans, khakis, or dress pants and cowboy boots, it’s best to keep it simple. Choosing a simple shirt or T-shirt can create an effortlessly stylish look.

You don’t have to make your outfit complicated with fancy or bright-colored tops. Just keep it simple and minimalistic.

Image copyright Tecovas Boot Company | #CommissionEarned | Tecovas Tops

A clean, simple shirt or T-shirt lets your cowboy boots be the center of attention in your outfit. This approach not only makes for an easy-to-put-together outfit but also shows off a classy and simple style.

Remember, elegance often comes from simplicity. By choosing plain clothing, you let your boots and pants show their quality and style. This shows sophistication and confidence in your fashion choices.

How to Wear Cowboy Boots for Women

From the casual charm of jeans and shorts to the feminine grace of dresses and skirts, this guide showcases how cowboy boots can be paired with different types of attire.

The main idea here is versatility: women can wear whatever they want with cowboy boots.

Whether it’s for a casual day out or a more dressed-up occasion, cowboy boots offer a unique blend of style and comfort, making them a versatile choice for any outfit.

This guide is designed to inspire women to try out different styles, confidently pairing their favorite cowboy boots with arious clothing choices.

Jeans – Skinny Jeans, Bootcut Jeans, Short Jeans, Flare Jeans

Jeans are the love of cowboy boots, jeans are always the number one priority for both men and women.

1. Bootcut Jeans

Bootcut jeans come into focus again as the perfect option for women who want to match something with cowboy boots.

These jeans are specially made to complement the body shape. They fit snugly around the hips, buttocks, thighs, and upper calves, and then gently flare out from the knee to the bottom.

This unique cut not only ensures a seamless fit over your cowboy boots but also highlights your curves in a stylish and attractive way.

Bootcut jeans are designed to work incredibly well with cowboy boots.

Their slight flare at the bottom provides enough room to easily tuck in the shaft of the boots, while the fit through the upper part of the jeans accentuates your shape.

This ideal combination of practicality and style makes bootcut jeans the top choice for women pairing them with cowboy boots.

Again, bootcut jeans prove themselves the top pick in the denim world, especially when it comes to complementing the classic appeal of cowboy boots.

2. Skinny Jeans

Almost every girl’s closet is likely to have a pair of skinny jeans, and for a good reason. Skinny jeans, when combined with cowboy boots, create a youthful, lively, and captivating look.

Skinny jeans offer a snug fit that highlights your figure, and when tucked into cowboy boots, they create a sleek and seamless appearance.

This pairing is not just about style; it’s about making a statement. It speaks to a sense of boldness and confidence.

So, if you’re wondering what to wear for a day out, look no further.

Simply slip into your skinny jeans, tuck them into your cowboy boots, and you’re ready to turn heads while walking down the street.

It’s an effortlessly stylish outfit that is sure to attract attention and admiration.

3. Short Jeans

Pairing short jeans with cowboy boots is a style choice that exudes charm, youthfulness, and allure. This combination strikes a perfect balance between casual and chic, making it a popular choice for those sunny days out.

The Jamie Cowboy Boots | Click the image for more info on Tecovas

There’s something confident and trendy about this pairing.

The short jeans highlight the legs, while the cowboy boots add a touch of boldness and a dash of classic Western flair. It brings an eye-catching and comfortable look.

I believe that many girls won’t think twice about choosing short jeans to wear with their cowboy boots for a day out.

This outfit captures the essence of youthful beauty and freedom that so many young women love.

4. Flare Jeans

Flare jeans or wide-leg jeans are making a significant comeback in modern fashion.

When paired with the right top, like a cozy sweater or an elegant blouse, they can offer a stunning urban style that’s both trendy and sophisticated.

These types of jeans, known for their wider leg opening and flare, offer a refreshing contrast to the common skinny jeans.

The flare at the bottom of these jeans adds a unique visual interest to your outfit, and when combined with cowboy boots, it brings a different vibe to your look.

The boots peek out subtly from under the flare, adding a bit of Western charm to the ensemble.

Image copyright Tecovas Boot Company | #CommissionEarned | Women’s High-Rise Flare Jean

What’s especially great about flare or wide-leg jeans is their versatility. Pair them with a simple sweater for a casual, laid-back vibe, or dress them up with a blouse for a more polished, chic appearance.

They are perfect for creating a variety of looks, from a relaxed weekend outing to a more put-together style for an evening in the city.

Dresses

Wearing a dress with cowboy boots is a timeless part of Western fashion, blending femininity with rugged charm.

This combination is important because it represents the spirit of the West – a balance of elegance and toughness.

A dress softens the bold statement of cowboy boots, creating an iconic look that is both stylish and grounded in Western tradition.

It’s a timeless ensemble that celebrates the heritage of the West while remaining fashionably versatile and approachable.

Line dancing, weddings, parties, etc. cowboy boots and dresses can be found everywhere.

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

The feminine dress and cowboy boots will make everyone fall in love.

Tea-length bridal dresses, mini dresses, A-line dresses, midi dresses, maxi dresses and 1950s-style short dresses can be the main focus of this classic combination!

Skirts

Incorporating skirts into Western style with cowboy boots is essential for achieving a classic and versatile look.

This pairing effortlessly merges the boldness of cowboy boots with the femininity of skirts.

Whether it’s a flowing maxi skirt or a playful mini, adding cowboy boots creates an outfit that is deeply rooted in Western fashion yet adaptable for various occasions.

It’s a timeless combination that captures the essence of Western elegance and resilience, embodying a unique blend of strength and grace.

Whatever is in Your Wardrobe

The beauty of cowboy boots, especially for girls, is their remarkable versatility. The options for pairing these boots with different pieces from your wardrobe are virtually endless.

My advice? Dive into your closet and experiment. Try on your cowboy boots with various outfits – you might be surprised at the plethora of stylish combinations you’ll discover.

Leggings, for instance, paired with cowboy boots create a sleek, modern look that’s both comfortable and chic.

Shorts offer a playful, casual option, perfect for warmer days or a relaxed outing.

And don’t forget about flare pants, which can add a touch of retro flair while perfectly complementing the boots’ distinctive style.

Each of these choices, from leggings to flare pants, has the potential to be exactly what you need for a fresh, fashionable look.

Cowboy boots have a unique ability to transform an outfit, elevating everyday pieces to new heights of style.

So, take a chance, mix and match, and watch as your cowboy boots breathe new life into your wardrobe staples.

Related Questions

1. What do Cowboy Boots Say About a Man?

Cowboy boots say much about a man’s character — they symbolize liberty, allure, and confidence, occasionally tinged with a hint of arrogance. These boots empower men to stand out, embodying the courage to think differently, speak boldly, and act decisively.

More than just footwear, cowboy boots are a statement piece for their wearers. The elevated heels add to the wearer’s stature, projecting an air of pride and self-assurance.

However, it’s crucial to remember that true pride and confidence come from within. Cowboy boots are merely instruments that help men express their inherent qualities and showcase their unique personalities.

Not everyone embraces standing apart from the crowd, and not all have the boldness to seek distinction. But for those who do, cowboy boots are a confirmation of their individuality and a testament to their willingness to be different.

They offer a distinctive blend of poise, coolness, and a touch of nonchalance, all without creating barriers in social interactions. This is the subtle artistry that cowboy boots bring to their wearers.

Moreover, cowboy boots represent more than just style; they are a manifestation of beauty, history, and a bygone era. They carry stories and traditions, making them not just a fashion statement, but a piece of cultural heritage.

2. What Not to Wear with Cowboy Boots?

Not as lucky as women who can wear anything with cowboy boots, men need to be more cautious!

They can’t wear skinny jeans and shorts with cowboy boots like women. Also, guys won’t put jeans inside cowboy boots, which is the matter.

To explain this, skinny jeans and shorts are not a good choice when worn with cowboy boots for guys. This combination doesn’t give men the style they want but rather takes away their manliness, arrogance and balance. Sounds bad, isn’t it?

Besides, men should not put their pant legs inside cowboy boots. But if your work nature requires you to do this (horse riding, farming and ranching, etc) then you can do this tucking thing. But believe me, that combination isn’t that good in terms of fashion.

3. Where Should Jeans Fall on Cowboy Boots?

For the best look when wearing jeans with cowboy boots (bootcut jeans, straight-leg jeans, cowboy cut jeans, etc.), your jeans must cover their entire shaft.

Cowboy boots have a much higher shaft than other boots (11 inches to 14 inches), so you’ll need a pair of jeans that are longer than usual to fully cover the shaft.

The jeans should fall on foot (vamp) on the cowboy boots, slightly longer to cover the foot of the cowboy boots a little.

That will definitely give you a nice look!

4. Do Cowboy Boots Look Good on Guys? Why do Guys Wear Cowboy Boots?

That’s for sure, cowboy boots definitely look good on guys, if you are a man, you must have a pair of cowboy boots in your house.

Why? Cowboy boots have all accents in their structure: high heel, unique shaft, vamp motif, beautiful toe shapes (pointed toe, round toe, square toe,…), and leather sole with great click-cluck sounds.

That structure adds height, confidence, and a little swagger for your own style.

Cowboy boots not only give a sharp look but also provide mental excellence to the wearer – a real cowboy lifestyle.

But as we said, cowboy boots alone can’t give you all. You are the one owning those styles and charisma, and cowboy boots are just the tools for you to show off.

5. Why do Cowboys Wear their Pants in their Boots?

Because when a cowboy stuffs the pants inside the cowboy boot, the boot protects the pants from getting torn or dirty, muddy, etc.

Also, when riding, your pants can tear and get stuck into the saddle’s stirrup, causing them to tear more and put the cowboy in danger. Tucking cowboy pants into the boot can prevent this problem.

Cowboy boots with a sturdy and tall construction can protect cowboys and their pants from negative effects.

But as we said, when it comes to fashion, it’s not a good idea to put your pants in cowboy boots.

6. Do Guys Wear Cowboy Boots Over Jeans?

When it comes to fashion terms, absolutely NO, guys don’t wear cowboy boots over jeans.

Unless you ride a horse or work and want to protect your jeans from mud or debris, you won’t wear cowboy boots over jeans.

When you slip your cowboy boots into jeans, you will have a sharp look, but if you do the opposite, you will be like a teenage boy wanting to show off yourself. That’s not the purpose of wearing cowboy boots.

7. Should you Wear Socks with Cowboy Boots?

You should wear socks with cowboy boots as they can bring you many benefits.

Many types of socks today have very good arch, heel and toe support. This allows you to easily break in cowboy boots without going through the frustrating process.

Besides, the heavy work you are doing also becomes more comfortable when supported by socks. Many socks are moisture-wicking to keep the feet dry and comfortable all day long.

In short, you can have many benefits when wearing socks with cowboy boots.

Before you leave

Don’t hold back your imagination; let it run wild. Rock your cowboy boots with whatever feels right. It’s all about wearing what makes you feel good and true to yourself.

Remember, when you’re feeling your best, you can handle anything that comes your way, no matter how tough. Believe in your style, wear those cowboy boots with confidence, and you’ll be ready to take on anything.

Wishing you the very best on your fashion journey with your trusty cowboy boots right there with you!

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!