Cowboys — they’ve been cool for decades. Whether you’re an old-school cowboy in the style of John Wayne and Angie Dickinson or a newfangled rancher like Shakey Graves and Esme Patterson, you’re sure to turn heads with your unique, old-school fashion sense.

How to Wear Cowboy Boots With Ultimate Style

That is if you know how to wear cowboy boots.

The fact of the matter is that not all cowboy outfits were created equal. Cowboys can be cool just as often as they are lame. You don’t want to be that person out who looks like they raided a costume store.

So what’s the solution?

Well, everyone can hide a poorly placed cowboy belt, western shirts are rather popular, and you can pass a cowboy hat off as a joke. But there’s one piece of cowboy wear you can’t get around if you wear it incorrectly — the cowboy boots.

The bold choice to wear cowboy boots in the 21st century can pay off. But you have to get them exactly right. This article will walk you through all you need to know about wearing cowboy boots.


If you’re a cowboy in the modern world, jeans are your first go-to. They’re so popular as to have become ubiquitous, and yet they have the durable, functional look that makes cowboy’s so unique.

Use the Neutrality

Jeans in everyday life are pretty neutral, they’re so popular you almost don’t see them. The same pair of blue jeans can look conservative, rock-and-roll, rockabilly, cowboy, urban, or chic, depending on the context. It’s your job, as a fashionable individual, to dress them up in a way that makes your style pop.

But it isn’t just enough to wear jeans with cowboy boots, you have to know how they fit together.

Don’t worry about flashy colors, embroidery, or ripped jeans. The boots are such a bold fashion statement, that it’s best to let jeans’ neutral appearance work in your favor.

Instead, tie your look together with a nice cowboy belt. You can go with an old-school belt with a large belt buckle or even a nice-looking leather belt that’s distinctively western. The space between the eye-catching boots and belt will provide a visually pleasing effect.

A great way to think of it is like the theatre. If someone is looking at your body from top to bottom, give them something impressive to look at, then give them a little intermission, then give them a finale — the boots.

Act Two

To follow this metaphor up, don’t connect your nice flashy belt with a gaudy western shirt. This will look forced on anyone but John Wayne. Instead, wear a simple, one-colored button-down, henley, sweater, or T-shirt.

Finish up your outfit with a distinct necklace, bracelet, or hat. You’ve gone neutral on your shirt, so you can go over-the-top here if you want. You can even wear a bolo tie, to double down on the cowboy look.

We don’t recommend putting all of these things accessories together, however, lest you look like you’re cosplaying The Hateful Eight. Pick one that you like, and go for it.

If you follow all of these steps, you’ve created for yourself a stylish, unique, balanced outfit with boots. People will be impressed and attracted to the unique features, but not put off by over-the-top showmanship.

Nice going, cowboy.


But jeans aren’t the only great piece of clothing that gives you many options for cowboy boots. For the cowgirls out there, here’s a brief rundown of how to wear boots with a dress.


If you’re wearing boots with a dress, the name of the game is contrast. If you’re wearing a white dress, blue, or red dress, wear black or brown boots. If your dress is darker, wear boots that are more bright, like red and blue.

The outfit to wear will turn out differently depending on if your boots turn out bright or dark.

Dark Boots

If you go with the dark-boots-light-dress option, your outfit will turn out a lot like the above outfit suggested for jeans. You’ll want to avoid a belt since the dress will most likely catch eyes, but you can certainly go with a necklace, bracelets, or hat.

A great option for women wearing boots beneath a light dress is to wear a denim or leather jacket. This gives a distinct, modern, rock-and-roll cowboy look.

Bright Boots

Bright boots are a bold statement, and you need to rock them. Say you wear red cowboy boots with a dark outfit — you’re going to send out a certain message that you’re confident, and not easily intimidated.

Consider pairing this with shorter, more daring dress styles, and darker makeup. Don’t worry too much about other accessories. The boots will announce your presence on their own.

Quality Boots

This should go without saying; you need a good pair of boots. All of the style tips listed above mean next to nothing if the books you wear look like something out of a middle school production of Oklahoma.

The best way to assure that you get a quality pair of boots is to make sure you shop with a reputable seller. You could go shopping in person, but not many places sell a wide variety of Cowboy Boots, and shopping in person amid the pandemic is still dangerous and tedious.

If you’re looking for a quality pair of cowboy boots, online shopping is the best option for you. Many online sellers, like Tim’s Boots, are able to make boots their specialty, so they provide many different types of boots, to suit many different types of boot styles. Click this link to find out more.

Whether you’re new to the vintage western style or have rocked the cowpoke style for years, quality is important. A cowboy wouldn’t skimp out on their material. You shouldn’t either.

Learn How to Wear Cowboy Boots

Cowboy boots are a fashionable option that perfectly mixes the rugged with the ubrane. Many people these days don’t know how to wear cowboy boots, and that’s a shame.

However, once you’ve found yourself a nice, neutral pair of jeans, bought a nice belt, figure out your accessories, or found a contrasting dress and fitted it accordingly, you’re well on your way to turning heads in your new cowboy boots.

For more articles, check out our fashion section!

Leave A Reply