How to Wear Cowboy Boots

Cowboy boots have been around for centuries. And cowboys aren’t the only ones that wear them—they’ve been worn by celebrities, royalty, country music fans, and just regular folks who like the look. 

These classic boots have stood the test of time, but the trend only continues to evolve. And if you just bought yourself a pair, you might be wondering how to wear cowboy boots.

With their chunky design and rugged look, many people believe these boots are difficult to style. Many might also worry that they’ll look like a typical rogue from 19th century Texas, or like a country bumpkin! But this isn’t true. 

There are so many styles of cowboy boots these days, including lots of chic designs. And learning how to wear cowboy boots is really easy.

With the help of this guide, you’ll be ready to rock your cowboy boots in style. In this article we’ll discuss the following:

  • How to wear cowboy boots without looking country 
  • How to make chunky designs work in your favor
  • How to style cowboy boots with different outfits
  • What not to wear with cowboy boots

Once you know how to wear your cowboy boots the right way, you won’t be able to get enough of them. So let’s get started.

What Is A Cowboy Boot?

The cowboy boot has been a popular fashion accessory since the early 20th century. The boots were originally meant for working boys who herded sheep, took care of horses and cattle, and also engaged in some menial labor work including fencing and building.

The boot provided these workers with the best support, grip, and comfort on busy days. In the early-to-mid 20th century, many Hollywood starlets donned fancier versions of cowboy boots in their movies.

One of the first celebrities to adopt this trend was Marilyn Monroe. In 1951, Monroe was seen wearing a pair of black cowboy boots with a two-piece outfit in a photoshoot, which immediately hyped up the footwear. 

The actress also wore cowboy boots in a couple of her movies. In 1954, she wore them in River Of No Return and again in The Misfits, which was released in 1961. Soon afterward, the cowboy boot quickly turned into a fashion must-have and was seen almost everywhere—worn by men, women, and kids alike.

Nowadays, there are many designers, such as Acne, Pierre Hardy, and Isabel Marant, that are still making cowboy boots. And each time they come out with a new design, they redefine their appeal, ensuring they never go out of style.

History of Cowboy Boots

The cowboy boot is a traditional riding shoe that was worn by cowboys and horse riders back in the early 16th, 17th, and 18th centuries.

They were usually made up of leather and handmade in a variety of styles based on their place of origin. Each region developed slight variations in design, adding to the novelty of the shoes back in the day. 

It’s said that the cowboy boots were inspired by the Vaquero boots which came to the Americas via Spain in the late 1600s. The original Vaquero boots were sturdy, tall, and had designs on them which added a bit of weight to the shoe. Also practical, these features helped maintain a firm grip when worn. 

During the American Civil war, the military boot (also known as the Wellington) overshadowed the cowboy boot for some time, since it was mass-produced and easily available back then. But soon after the wartime was over, the Wellington boots disappeared and were again replaced by cowboy boots.

Later, as times evolved, the way that shoes were produced changed drastically. Instead of being handmade, cowboy boots were mass-produced by the newly opened factories and corporations. It was suddenly extremely easy to get access to a pair, which also contributed to the popularity of the shoe.

But if you’re still wondering how the early cobblers made their cowboy boots, you can travel to the Wild Wild West and see for yourself! There are still cobblers operating in Texas who could show you real, authentic boot-making techniques, which were passed onto them by their ancestors.

So you’ll get to see how the boot was made in the past. Intriguing, isn’t it?

When to Wear Cowboy Boots

Today, with so many retailers making them, you have access to cowboy boots in a variety of styles. You can either opt for a classic tan pair, a patterned style, embroidered boots, or even a fringed pair—which might awaken the inner Texan in you!

Over a century ago, cowboys used to wear these boots every day but, in modern times, that’s not the case at all. Of course, you cannot wear fancy cowboy boots as everyday-wear shoes. 

But the classic pairs in basic colors, such as black, tan, and beige can be worn with almost any outfit on most occasions. So, if you want to keep your look classy and chic, and avoid any fashion faux pas choose one of these styles.

In recent years, many trendsetters have been spotted wearing patterned or embroidered cowboy boots for fancy events like fashion shows, movie premieres, and parties. Since these types of cowboy boots are bold and attention-grabbing, it’s a good idea to reserve them for special occasions.

The classic pairs in basic, neutral colors are much easier to style, which makes deciding how to wear cowboy boots pretty straightforward.

How to Wear Cowboy Boots

Learning how to wear cowboy boots fashionably is important for many. The most important thing people wonder about when they buy a pair of cowboy boots is if they go over their pants or under them? The answer is, both! 

So how can you pull this rugged look off and look fabulous? Read the style tips below and find out.

For Women

While wearing flared pants with women’s cowboy boots was a big trend in the ‘70s, it’s a rather difficult look to pull off these days unless you’re blessed with some good height.

So, if you’re a tall person, it’s a great idea to pair your cowboy boots with some flared pants. And, in this case, you can wear your boots underneath your pants and you’ll look great. 

But, if you’re not blessed with a tall figure, we recommend that you get a pair of cowboy boots with a platform-heeled sole. The heel will add some extra height, elongating your silhouette nicely. And you’ll look fantastic wearing a chunkier-style shoe.

On the other hand, if you want to wear your cowboy boots over your pants, the options are limitless for you. You can easily wear these boots with jeans, leggings, skirts, shorts, and even dresses. And, with so many style options, deciding how to wear cowboy boots becomes oh-so-easy.

For Men

If you want to wear your cowboy boots with jeans, it’s important to consider the length of the jeans. Your jeans need to be just the right length and shouldn’t cover your boots completely. 

An ideal pair of jeans to wear with cowboy boots would be those that cover about 20-40% of the shoes while leaving the bottom part bare. This is an important point to keep in mind when buying men’s cowboy boots.

Here are the best styles of jeans that you can pair with your cowboy boots:

  • Regular Cut Jeans: This style of jeans looks great but you might have to bunch up your jeans if your cowboy boots have no extra space. That’s why it’s a good idea to grab a pair that are a size bigger than your regular size (if you want to wear them with boots).
  • Boot Cut Jeans: Pairing boot-cut jeans with cowboy boots was big in the ‘70s! This trend is still popular today and the most convenient. The jeans have a bit of a flare, which accommodates the chunky shoes and complements them perfectly. 
  • Skinny and Slim-Cut Jeans: Slim-cut jeans are also a popular option to wear with your cowboy boots. Wearing the same color of cowboy boots as your bottoms is an ideal option for those who are looking to create an illusion of extra height

10 Outfit Ideas With Cowboy Boots

Go bold by pairing a pair of printed women’s cowboy boots with a dress. This black pair are the Burberry Topstitch cowboy boots which were launched in the brand’s Resort 2020 lookbook. Cowboy boots go really well with dresses of all lengths and the options are limitless. 

Everyone and their mothers know that monochrome outfits are totally in these days, so why not pair your black leather cowboy boots with a leather outfit? This look is incredibly easy to style, and we’re sure you have a trusty, black leather jacket somewhere in your wardrobe. 

Pastel cowboy boots with intricate designs and embroidery are totally in vogue these days. And, if you ask us, this is the pair you need if you want to awaken the inner fashion blogger in you.

These patterned cowboy boots come in various colors and a host of patterns. If you’re not a fan of pastels, you can opt for a darker color instead

Let’s circle back to this OG trend. Back in the day, white shirts and cowboy boots were a staple in everyone’s wardrobe. Today, you can style your shin-high or knee-high cowboy boots with a statement white dress and tribal accessories for a classic bohemian vibe.

Statement women’s cowboy boots are the ultimate accessory and an immediate head-turner. Remember that if you’re wearing patterned cowboy boots, they need to be the focus of the outfit. Style your clothing in basic colors with patterned cowboy boots to create a fashion-forward look.

Pair your men’s cowboy boots with some flared jeans and a hat and you’ll look like you belong in the Wild Wild West! Even though this is a classic trend, it might be a little difficult to pull off.

To keep things simple, you can always choose monochrome attire to match your boots and take the least amount of risk possible. 

If you’re wondering how to wear cowboy boots without looking country, this is the way. 

Wearing a light-washed, high-waisted pair of jeans with cowboy boots will get you some extra brownie points from the fashion police! Just throw on a crisp white shirt or a printed tee and walk out in style.

Sometimes, when deciding what to wear with cowboy boots, you don’t have to overthink it. Just wear them instead of your sneakers one day and experiment with your style.

In 2022, cowboy boots are incredibly fashionable for men. And you should consider buying a plain black pair if you’re thinking about which type of cowboy boots you want to grab first.

Kids’ cowboy boots are popular because they’re incredibly comfortable and functional. They come in various styles and patterns as well. Get a colorful pair in bright colors according to your kid’s choice, and pair them with dresses, jeans, shorts, and skirts.

Kids love wearing cowboy boots and the classic tan pair would look great with almost anything. Just keep in mind that these kids’ cowboy boots might cause a blister when your little one is wearing them for the first few times. So wearing some thick socks is probably a good idea.

What Type of Cowboy Boots Can You Get?

The original cowboy boots from the past were extremely sturdy, and an ideal choice for the desert full of cacti and snakes. But the boot has evolved over the years and now is mostly worn for its style factor.

Let’s review the various types of cowboy boots you can find in the modern day:

  • Western Boots: Western cowboy boots have pointed toes, a one or a two-inch heel, and a tall boot shaft.
  • Work Boots: They have a short heel perfect for working on your feet all day.
  • Riding Boots: These types of shoes are very popular and are meant for horseback riding. They’re designed to provide you with the most amount of comfort when on the saddle.
  • Exotic Cowboy Boots: These boots are made up of animal skins, including alligator,  lizard, stingray, ostrich, snake, deer, and even eel skin—so take your pick.
  • The Fashion Cowboy Boot: These are the modern versions of cowboy boots that are meant for style, and less for functionality and comfort.

How to Choose the Best Cowboy Boots

Here are some tips that can come in handy when choosing the right pair of cowboy boots for yourself. They’ll make figuring out how to wear cowboy boots much easier.

  1. When you’re out trying on different pairs of cowboy boots, make sure to try them on with socks. This will help you find the perfect size for your feet.
  1. Some cowboy boots have a tapering, narrow toe so they might be a little small for you if you have wide feet. If you do, it’s best to opt for a wider pair that will have more toe room.
  1. You need to have at least a thumb’s width distance from your toes and the edge of the boot.
  1. You won’t know if the shoes fit snuggly if you try the cowboy boots when sitting down. So walk around, and make sure there’s enough wiggle room before buying them.

Fashion Tips to Avoid With Cowboy Boots

It’s a good idea to pull off a classic Wild West look but you shouldn’t overdo it with fringes and a large hat. When trying to pull off a Western look, some people immediately think of pairing overalls with cowboy boots but, truth be told, this clothing choice is absolutely overdone.

Don’t restrict your cowboy boots just for your flared jeans. Pair them with business casual outfits or monochrome outfits as well for an effortlessly modern look

Another mistake that you need to avoid is wearing cowboy boots with loungewear and athleisure wear. These two styles are polar opposites, and mixing the two together would bring you some fury from the fashion police.

Pairing feminine accessories (such as bows and ribbons) with cowboy boots is probably not a good idea either. When wearing accessories with cowboy boots remember that less is more. 

How to Take Care of Cowboy Boots

To maintain the look and the quality of your cowboy boots over time, it’s important to clean them regularly. Here’s how to take care of your cowboy boots to ensure that they last several years.

  • Use saddle soap or shoe cleaner to remove any stains on your boots. You can either clean them using a soft cloth or even a toothbrush if they’re excessively stained. Remember to be gentle. If your boots are made of suede, you need to use a dry-wiping cloth.
  • Condition your boots with a shoe conditioner. This helps maintain the look of the boots and ensures that they don’t dry out. Dry cowboy boots might shed the leather over time, so conditioning them is essential.
  • Polish your boots with shoe polish and voilà, they’ll look almost as good as new.

It’s important to clean your cowboy boots every couple of months or even once a month if you wear them regularly. Do this and your cowboy shoes might even last you a lifetime.

Best Places to Buy Cowboy Boots

Here are some of the best brands that sell cowboy boots. Check them out if you’re considering buying a stylish and sturdy pair this season.

  • Justin Boots: Since 1879, Justin Boots has been mastering the art of fine shoemaking. This is an old-heritage brand you probably won’t regret buying from.
  • Lucchese: This brand is known for designing cowboy boots for well-known individuals like Bing Crosby and all the members of the Dallas Football team.
  • Ariat: Ariat is a new brand that’s changing the face of cowboy boots with its emphasis on superior technology and innovation. You definitely need to check out this brand if you like to stand apart from the crowd.
  • Soxy: has a host of designer cowboy boots from luxury brands like Maison Margiela, Ganni, Golden Goose, MSGM, Isabel Marant, and more. 

Final Thoughts

Cowboy boots are definitely here to stay, and you need to make them a part of your wardrobe this season! The main point of fashion is to have fun, and a pair of cowboy boots will add an edge to any of your outfits. 

Get a pair of classic boots or any of the new styles to elevate your look and make sure to clean them regularly so that they will last a lifetime. 

In the end, how you wear cowboy boots and jeans is a matter of personal taste, but with this helpful info about the right length, cut, and styles you’ll be in a better position to get started. We hope you find your perfect fit!

Wondering how to style other types of footwear? We’ve got you covered:

How to Wear Ankle Boots With Jeans

How to Wear Booties With Jeans

How to Wear Converse

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