Man Pushing the Accelerator Using Cowboy Boots.

The epitome of Western wear – the famous cowboy boots have a special place in American culture. They’ve been worn by everyone and anyone, from presidents and country singers to ranchers and cowherds. The fine blend of functionality and unique style has cemented Western boots as a staple of American (and global) fashion. Yet, even after centuries of use, the same question still comes up: how to wear Western boots the right way? What to pair them up with? What goes best with cowboy boots?

Why, you may ask? Well, the manifold styles and models of Western boots make it hard to generalize them in terms of fashion rules, and the accompanying clothing has changed over the years. Do you wear traditional cowboy boots? Or are you wondering how to style a typical cowboy work boot or western ankle boots with your favorite outfits?

Let's dive right into our cowboy boot style guide to answer some of the burning questions weighing on your mind and help you style them with ease for any occasion. Find out how to effortlessly rock this iconic footwear!

What Makes Western Boots Special?

First off, the history. When you put on a pair of Western boots, you are continuing a centuries-long tradition. The first western boots were designed to be functional, cheap, and durable boots that cowboys could wear to work. They were as functional when riding as when walking. In a short time, their popularity skyrocketed. Western boots were no longer just meant for the ranch but became everyday footwear.

Then, the designs started becoming much more elaborate until you get to the modern versions – you'll be hard-pressed to find a basic western boot with no special patterns or decorations.

Timeless Functionality

A key reason to wear cowboy boots is their functionality. Even with the evolution that Western boots have undergone, they still serve their original purpose – comfortable and durable boots that will get you through thick and thin. Regardless of whether you'll wear them to work or to the pub, you won't lack comfort and protection, especially if you opt for USA-made boots, which are a testament to traditional top-tier craftsmanship.

The Talk of the Town

We can't talk about cowboy boots without mentioning their unique style. If you believe that your personal style reflects your personality, there's no footwear quite like Western boots. You can wear the most expensive boots in the world, but they won't make a statement like cowboy boots do.

Cowboy boots are instantly recognizable and radiate authenticity. Some people may like the fashion statement you are making while some may not, but one thing is for sure – they will notice and remember you. Unless you are at an Old West-themed festival, showing up in cowboy boots is bound to make you the center of attention.

Western Boots

The Evergreen Heel Addiction

Finally, we have to talk about the heels. It may not seem like a big deal, but once you start walking and hear that distinct click-click-click sound, it'll be like every other cowboy is cheering you on. Plus, let's not forget the few extra inches you get. The sound you make when walking and the added height will boost your confidence to new levels.

Different Styles of Cowboy Boots (And When & How to Wear Them)

If you are wondering how to wear western boots in style, you first need to get acquainted with different types of cowboy boots. Different styles still have the same distinct look, but you should still know what you've got on in order to choose the right stylish clothing to follow.

From Subtle to Sensational

The most noticeable element of Western boots is the stitching. You can find relatively plain, basic boots (at least compared to other Western boots) to Western-inspired boots so elaborate in their decorations and exotic leather designs that they would even make a burlesque dancer blush. If your boots are on the safer side, you can go wild with the rest of your outfit. If you go for an intricately designed boot with embellishments, play it safe and at least wear a simple pair of pants in a neutral color.

Toe Shape

Then, we get to the toe shapes. Western boots are usually thinner than other boots and have a distinct taper at the end – this gives them their unique look. Besides the traditional, thin-toe style, you can also find boots with a more rounded or even squared toe, known as box-toe boots. These features add some variety to the look you can go for, but they still have the same overall distinct appearance.


Finally, we should discuss the height. Authentic cowboy boots are usually around 10-14 inches high. So, they rarely go below the mid - calf. Modern cowboy boots have shaken things up, resulting in an array of tall cowboy boots. You can now come across ankle-high and even knee-high cowboy boots.

Cowboy Boot Styling 101: What Goes Well With Western Boots?

Now, we get to the core of the article – what to wear with western boots.

First things first: the general rule of thumb to stick to is one Western item per outfit. Unless you are an actual cowboy on a ranch or going to a western-themed festival, there's no reason to add anything to your boots. So, no cowboy hat, bolo tie, or spurs. Whether you go for ankle-style boots or tall cowboy boots, a pair of cowboy boots makes enough of a statement on its own without any additions.

Now that we’ve got that covered, let’s talk Western fashion.

Western Boots

The Classic Cowboy Boot Look: Pairing Western Boots with Jeans

Your safest bet when looking for a classic style and casual wear? A pair of trousers. Marry a good ol' pair of jeans with cowboy boots and a collared simple t-shirt to make your outfit simple yet stylish in true American fashion. Oh, and don't forget an oversized blazer for maximum impact and a classic country vibe! This way, you'll still stand out because of your cowboy pair of boots but look fashionable while doing it.

You could try to pull off the iconic Bruce Springsteen look – your favorite pair of classic boots (western style of course), dark blue jeans (pro tip: go for boot-cut jeans or straight-leg jeans), and a plain white T-shirt. Top it off with a leather jacket for a casual classic staple or an oversized jacket for a more modern look.

Or go crazy and double the fun with double denim! These looks have an edgy vibe to them and would for sure turn some heads at a country music festival, but it's not ideal for more formal social occasions. And, finally: Do you tuck your jeans into cowboy boots? Well, it's all about personal style. Tuck your jeans into your boots for a sleek and polished look, or let them fall over the boots for a more relaxed and casual vibe.

The Formal Western Work Boot Look: Suiting It Up

A riskier look and a bit more difficult to pull off is the cowboy formal. You've guessed it – we're talking about pairing cowboy boots with a suit! However, if wearing Western boots with business wear is your fashion of choice, make sure the suit is casual and the pants are wide enough so that the boot shaft doesn't make a bulge. And don't tuck your pant legs into your boots, even if wearing an ankle cowboy boot if you’re at a formal event – ever.

In more urban areas, throwing on a simple jacket or blazer with cowboy boots is a great choice. A denim jacket also always goes well with Western boots and balances the look. Adding a nice leather belt will complete the outfit and can turn your style from casual or overly country to semi-elegant.

Wearing Shorts with Cowboy Boots

Looking for some chic cowboy-boot outfits? Then pairing Western boots with shorts is a no-brainer! Who says you can't look effortlessly chic while strutting your stuff in a pair of Western boots? Whether you opt for a casual t-shirt and denim shorts combo that screams "effortless cool," or you dare to push the fashion boundaries with trendy bike shorts, one thing's for sure - you'll be turning heads and leaving a trail of style envy in your wake.

So, embrace the unexpected, and prove that pairing cowboy boots with shorts is actually a match made in sartorial heaven. Ride the waves of Western fashion with confidence, flair, and a hint of rebellious spirit. Remember when we said one Western item per outfit? While this is generally a good rule of thumb to stick to, like everything in life, it's not set in stone.

After all, it's your style, and you should do what you want; overemphasize your Western style as much as you want – dress in all denim and put on a cowboy hat, too. Just know that wherever you go, it'll scream cowboy.

Women's Western Boot Style Guide: Styling Cowgirl Boots Like a Pro

Yeehaw, ladies! It's time to saddle up and join the cowgirl fun because, let's face it, girls love western boots too! From fierce fringe to intricate embroidery, these boots are made for walking and slaying. So, trade in those stilettos for some sassy cowgirl kicks and let your inner rodeo queen shine in a Western vibe.

Unleash your inner cowgirl and show off some skin while sporting the most coveted footwear of the wild west. Saddle up as we unveil top tips on how to effortlessly pair your favorite cowgirl boots with dresses, skirts, and more.

  • Pair your favorite cowboy boots with flowing maxi skirts for a boho vibe and a chic look that's both effortless and stylish.
  • Embrace a flirty and feminine vibe by wearing slip dresses with cowboy boots, creating the perfect balance between Western flair and modern elegance.
  • For a fun and playful outfit, rock a mini skirt with bright boots, channeling a hint of country charm into your urban chic ensemble.
  • Elevate your fashion game by combining a classic slip dress with a pair of black cowboy boots, creating a unique blend of vintage allure and Western edge.
  • Unleash your inner cowgirl boss by donning a shirt dress and completing the look with a confident pair of statement boots, exuding a perfect mix of ruggedness and sophistication.

cowboy boots shoes and hat with pink roses

A Few Key Things To Remember When Wearing Cowboy Boots

To sum it all up, let's pinpoint some of the key takeaways and answer some of the most frequent questions about when and how to wear Western boots:

  • Do You Wear Cowboy Boots with Socks?

Absolutely! Socks provide comfort and prevent blisters, so don't forget to wear them with your cowboy boots.

  • When Should You Not Wear Cowboy Boots?

There are no rules, but consider avoiding wearing them during formal black-tie events where dress shoes are more appropriate unless you really want to stand out. After all, in their essence, cowboy boots are casual footwear. So, don't wear them to business events unless you live in Texas or work in the oil industry. However, they are the perfect choice for any fun social events such as fairs, festivals, bars, and concerts.

  • How Not to Wear Cowboy Boots?

Avoid mismatching styles or overdoing it with too many Western-inspired elements. Keep it balanced, and let the boots be the statement piece.

  • Most Imporantly, Be Yourself!

Of course, based on the color and decorations of your favorite boots, you may or may not fit in, no matter the event. To paint a better picture, think of pure white cowboy boots with American flag decorations. Such Western-inspired boots will stand out wherever you go, regardless of the rest of your outfit. However, that may be exactly where you're getting at. Fourth of July, anyone?

So, do what you want and show off as much as you like, as long as you feel comfortable. “Proper” and acceptable fashion choices are subjective, after all. Buck their expectations if you feel like it!

Get Your Howdy On: Shop for Premium Western Boots Today

If you've been a sneaker or traditional shoe man your entire life, it'll feel a bit strange the first time you put on Western boots. Don't be discouraged – as soon as you start walking and hear the distinctive click of the heels, you'll be amazed at how much more confident you feel.

We won't go so far as to say that you'll be an entirely new man once you put on cowboy boots, but we will say that your attitude will change. You'll be carrying on a proud tradition of hardy and strong men and it will be evident in your walk.

At Overlook Boots, we've got the widest Western boot selection from the leading boot brands that offer unparalleled quality in true American tradition spirit. So, go ahead – browse away to find your favorite pair. Then, put on some bleached jeans, denim shorts, a dress, a skirt, or whatever your inner fashionista desires, and go show off your new look around town!