Cowboy boots aren’t just a fashion statement – they can be a surprisingly functional option when it comes to boots. They have been worn by actors, Presidents, businessmen, and a whole host of others who understood what made them so unique: and now, even though they might not be as popular as they used to be, cowboy boots can still offer something special.

If you are considering trying to wear cowboy boots for the first time in your life, it is important to get it right. Like any clothing, knowing how to wear cowboy boots comfortably and safely is the only way to ensure that you’ll get the right kind of experience. Want to know how to wear cowboy boots properly? Here is our quick guide on how to make full use of the style cowboy boots can offer.

Why Wear Cowboy Boots?

Cowboy boots can seem like quite an odd choice at first, especially if you haven’t tried to wear a pair of cowboy boots in the past. It can be difficult for many people to see the exact appeal of cowboy boots as a whole, especially compared to cheaper and more practical shoes that might be more readily accessible. However, for certain people, it becomes obvious as to why they should wear cowboy boots, especially if they can find a pair that perfectly suits their situation and needs.

The shape of most cowboy boots is part of the reasons they are so loved: they are distinctive and carry a style that most people can recognize immediately, making them stand out. However, they don’t stand out in a bad way, unlike other shoe options that might force people to pay attention with bright colors or large extra layers.

Additional height can be another popular reason to wear them: while most cowboy boot types will only add around one inch in height, some can even add two whole inches, and others can reduce it to a half-inch. This means that smaller men and women can get some extra height in a way that looks natural and blends in with the rest of their outfit. Many people might even wear cowboy boots specifically because it can make them look taller.

Know the Styles

Many people think that “cowboy boots” are all one specific type, but there are actually quite a few designs of western boots, each of which is slightly different. For example, Stockman cowboy boots are shorter and wider at the heel than a standard cowboy boot, whereas Buckaroos are much taller and generally designed to be flashy. In the middle, you can have types like Ropers, which are built for rodeos and offer a more rounded toe.

All of these styles are generally minor differences to one another, and most western boots follow the same overall shape and style. The most important thing to consider when buying a pair of cowboy boots is the amount of visual clutter: while many designs are meant to look like conventional cowboy boots with very little extra material, others are far showier and use fake gems or multiple colors of leather.

Decoration of cowboy boots can be a huge part of the appeal, especially when it is needed for a semi-formal event or some kind of celebration. You can get cowboy boot designs in almost every color imaginable, and there are thousands of options out there to choose from.

Choose a Size

There isn’t much special about cowboy boots when it comes to sizes, but people who don’t wear boots often can still easily be caught off guard. Most cowboy boots need both shoe size measurements and width measurements to be worn correctly. In most cases, cowboy boot designs can have widths between A to EE. Women’s boots are sized at around A to C, and men’s boots generally go from B to EE, although there is some overlap, and certain designs don’t follow this structure.

In the same way, some boots have thicker soles and heels than others, which can add height to the user. If you are a taller person, you will probably want to avoid cowboy boots with a two-inch heel, since this adds even more to your height than you might be comfortable with. On the other hand, if you are quite short, a small half-inch heel in your cowboy boots won’t help counteract that very much.

What to Wear with Cowboy Boots

When you wear cowboy boots, the rest of your outfit matters a lot. Not only do certain fashion options not work quite as well, given that the boots have taller designs and wider necks, but it also comes down to style. Western cowboy boots can seem quite difficult to dress properly for, and the ‘look’ that you end up creating isn’t always going to have the same kind of style that you expect. Wearing cowboy boots properly requires some careful thought on what you can wear while still looking stylish.

It is important to make sure that your entire look doesn’t revolve around the fact that you are wearing cowboy boots. Yes, cowboy boots can be an appealing item of clothing in many cases, but that doesn’t mean that a pair of boots should be your central identity. In fact, deliberately choosing a look to downplay how your pair of boots looks can be a good idea. Either way, you want to look comfortable and confident, whatever that takes.

You can pair nearly any item of clothing with western cowboy boots. You just need to put some effort into building up a consistent style. The only thing worse than an unappealing outfit with cowboy boots is an outfit with completely mismatched cowboy boots, especially if they really don’t fit.

Shirts

Collared shirts are usually the most appropriate options for pairing with cowboy boots if you want to appear stylish. However, you can also use a t-shirt without looking too out of place as long as you are in a very casual setting. If you are stuck for ideas and don’t know what you should try to pair with your new boots, consider a regular white dress shirt – it won’t look too fancy, but it can fit with any kind of cowboy boots and won’t appear too casual or formal for most events.

If that is not quite enough, you can easily swap to patterned shirts instead. The look will be different, but it will pair with your cowboy boots in exactly the same way, ensuring that you always look at least acceptable. Again, patterns can sometimes work on t-shirts, but the overall look and style of a t-shirt make it less desirable overall.

Jeans

Jeans are some of the most commonly-worn pants when it comes to cowboy boots, and it is easy to see why. Most jeans are thick enough to fit around the neck of the boots, and they can be a distinctly western item of clothing that works well with other items in that same style. Ideally, darker jeans are the best, preferably close-fitted ones that don’t appear to be too loose.

Avoid the light blue work jeans that you might see quite often. These work for quite a few outfits, but not when cowboy boots are involved, and the blue of the jeans can often go against the style of the boots themselves. The jeans you wear with cowboy boots can easily vary, but you should never tuck them into your boots unless you are going to be doing an activity that requires it.

Remember that most jeans are also a good option for regular, street style clothing. You probably already own some jeans that would fit, even if they are not the exact fashion you might expect to wear with a pair of western cowboy boots.

Belts

If you are wearing jeans, belts can often be the best way to complete the style that you are aiming for. A large buckle and decorative leather can be a great way to cap off otherwise bland-looking jeans, and you might even end up creating a custom buckle that adds a personal touch to your style. Other than that, there isn’t much to say about belts, since a lot of them can look similar enough to replace each other with nobody noticing.

Formal Clothes

Wearing cowboy boots with dresses or formal suits is quite a common sight, especially in areas that still have that western touch, and you can also use boots like this for formal occasions without sticking out too much. Cowboy boots with dress trousers are quite a common sight at events like weddings or parties, and choosing to wear cowboy boots in this way doesn’t invalidate the tone that you are going for. For example, you might wear a simple white suit and matching western boots to get a design appropriate for a wedding or choose all black if you want to blend in with the crowd a little more.

Tweaking your style enough can make almost any item of clothing work. Turtleneck sweaters and dress clothes might look completely different, but the right combination of cowboy boots, dress trousers, and careful use of accessories can make them work surprisingly well, regardless of your preferred style or color.

Trying to pair cowboy boots with a dress can work surprisingly well for women, although it depends on the dress type. Some people will look better in a shorter dress that doesn’t quite reach the knees, whereas others may look a lot better with one that actually covers the boots: either way, most dress types can work, although a cowboy boot/dress combo isn’t always going to fit with every event you might need to attend.

Jackets

If you want to dress with a more professional or focused style, a good jacket can complete your look quite easily. Sports jackets are good if you want to keep that formal look while wearing your boots, but you can also switch over to denim or leather for something that is not quite as restrictive and limiting. Some people also prefer the look of a long trench coat, but full leather dusters – while distinctly western – can look really out of place in most modern locations.

Remember that jackets make it impossible to see your shirt from the back, meaning that the rest of your outfit will need to compensate. If your jeans and jacket only look right when your shirt is visible, you have done something wrong: a jacket should match with your shirt and your jeans well if possible, especially if you plan to pair them together quite often.

Hats

It can be very tempting to wear a matching hat with your cowboy boots, but unless you are really trying to push the idea of looking like a cowboy, you should avoid it. Cowboy boots are already one item that many people won’t wear, and choosing to pair that with a hat that also stands out can double the impact it has. This isn’t always a good thing, though, and it can make people see your outfit as a costume – perhaps even a bad costume.

If you really want to go for a hat, try to find one that would pair with your outfit normally anyway. A cowboy hat is an obvious choice that just screams ‘cowboy’ at anybody who sees you, but if the hat could already pair with your jeans and jacket, it doesn’t become as severe. Going for a different kind of hat altogether and skipping the cowboy stereotype can also be effective, but it depends on how well it matches the rest of your clothing.

Where and How to Wear Cowboy Boots

Most of us know how to wear cowboy boots, but that doesn’t mean we all know where to wear cowboy boots, or how we can make cowboy boots look good regardless of our outfit. First of all, there are some places where it can be risky (or even inappropriate) to wear boots unless they are part of your known style:

  • Political events.
  • Serious presentations.
  • Modern dance clubs (especially if you plan to dance).
  • High-end theatre or musical performances.
  • Long drives and hikes.
  • Solemn events (such as funerals).

If you are known for wearing western boots like this, you will be much more likely to get away with it, since people know that you like them. If you haven’t worn your boots in public yet, wait for an appropriate time and place. These can include:

  • Bars.
  • Comedy shows or other smaller performances.
  • Music concerts, especially outdoor ones.
  • Country events.
  • Casual restaurants.
  • Horseback activities.

Of course, this is just a small selection of possible places you could wear your boots. The way that you build your personal style of boots, as well as the other clothing you wear alongside the boots (such as western-style jeans or a western hat), can play a role here too. If you can’t wear classic jeans at a formal event, then it might ruin your outfit if your boots needed the jeans to tie it all together. At a certain point, it becomes more convenient to simply change your outfit altogether rather than trying to salvage something you can’t wear properly (due to dress codes, the host’s rules, or other restrictions).

Remember that most cowboy boots are generally large and attract some attention, too. If you haven’t shown off the boots before, they are going to put a lot of eyes on you the first time people see you wearing them, especially if they didn’t seem like something you would own. Try to choose a good time to reveal them: for example, you might want to avoid wearing them for the first time at a birthday party or wedding, since this takes attention away from the hosts or subjects of the event.

About the Author

Hey, I'm Lilly Harvey. If there's two things I'm passionate about in life, it's shoes and writing!

Combining both my passions with my Fashion Design degree, I've helped create Shoe Adviser to help readers choose the best shoes for them, enjoy!

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