Men’s Jeans With Cowboy Boots: How To Wear It Properly

Are you new to the realm of wearing jeans with cowboy boots? Or perhaps, you’ve seen a pair of boots in a shop window, and aren’t sure what to do with them after you get them home?

You may even be wondering if you can wear skinny jeans with cowboy boots. And, that’s okay, because today we’re going to answer some questions about wearing cowboy boots with jeans.

Here is a quick look at the questions we will be answering:

  • Can you wear skinny jeans with cowboy boots?
  • How do you wear jeans with cowboy boots? Are some styles or cuts of jeans better suited than others to be worn with cowboy boots?
  • Are you supposed to tuck your jeans into cowboy boots?

Can You Wear Skinny Jeans With Cowboy Boots?

The answer: Absolutely! This is a perfect option for a pair of boots with a beautiful upper that just needs to be shown off. Maybe the stitching perfectly matches your shirt, maybe they’re hand-tooled and just drop-dead gorgeous. Maybe they’re made from exotic material. Or, maybe, you just really like them.

All of those are good reasons to show them off and skinny jeans are an effortless way to make that happen.

How Do You Wear Jeans With Cowboy Boots?

Boots and jeans were made for each other. It’s a combination that’s as well known as football and tailgates, peanut butter and jelly, mac ‘n cheese, or a toothbrush and toothpaste. But not all jeans are created equal, and some cuts or styles are much better suited than others to be worn with cowboy boots.

Now, obviously, the size of the leg opening on the jeans will determine if or how they can be worn with jeans. The ever-popular “boot-cut”, as the name implies, will always pair well with a pair of jeans. That is because the leg opening widens slightly as it descends from the knee, allowing the jeans to be pulled over the top of the boots.

A smiling woman wearing bootcut jeans.

And while flare jeans would look ok worn over the boot, it is not appropriate for tucking into the boot, as there is just too much material for it to be done comfortably. Skinny jeans, on the other hand, will not fit over boots. The only option here is for the boots to go over the jeans.

If you are planning to tuck your jeans into your boots, skinny jeans (for girls), or narrower, straight-cut jeans (for guys) are your best option. This is often called a “cowboy cut” or “stackable straight”. The “stacking” refers to the folds created in the jeans when the leg is slightly longer than necessary and stacks up above the boot, whether tucked or left out.

The style of boot will also come into play here. A boot with a tall shaft is going to require a jean with enough material and a large enough leg opening for the jeans to be pulled down over them. This style of boot works well for tucking jeans into the boots.

Should You Wear Jeans Tucked Into Cowboy Boots?

Here is where it gets a little more complicated, at least, that is if you’re a guy.

For Men

Yes. And, no. Let me explain…

For men, jeans are only seen as generally acceptable to be worn tucked inside of boots (or “bloused”, if you’re looking for the proper terminology) in very specific circumstances. And basically, that means when you’re working. Or getting dirty. So, think of “functionality” here.

If you’re doing anything that might get your pants wet, muddy, or dirty, it is considered acceptable to tuck your jeans into your boots. For example, if you’re outside working cows and the pasture is muddy, that’s a good time to tuck your jeans into your boots.

If you’re riding horses through mud or tall grass or walking through a barn with fresh manure, that’s a good time to tuck your jeans into your boots. When you’re working out in the snow or rain, that’s a good time to tuck your jeans into your boots.

Protection is another reason for tucking your boots into your jeans. That includes protection from thorns, brambles, bugs, and snakes. For example: having to cross through a creek bed, or through heavy brush. Or, perhaps if you’re out building a barbed wire fence, or fixing a fence.

Cowboy standing in the field.

Having the boots on the outside prevents your jeans from getting snagged. It also makes it a little harder for insects, like tics, to find their way up your pants leg. And the leather uppers are good protection from that startled snake that you didn’t notice in all that tall brush. It also helps keep poisonous plants like poison ivy and poison oak from finding their way up your britches.

You will also often see construction and oilfield workers with their boots over their jeans. Although, most of the time, they wear their kind of half-in and half-out, usually with the inside half of the pant leg tucked in and the outside half left out.

The reason for this is that they usually just pull their boots on and go, causing the jeans to initially just bunch up and rest on the top of the boot. As the day progresses, the pant legs may (or may not) fall inside the boot. This has a surprise advantage, though, and that is a little extra airflow around the legs, which is a blessing when you’re working outside in hot weather.

As for formal occasions, boots should be worn on the outside of jeans. The primary reason, here, is that tucking dress pants into boots would result in bunched-up fabric, along with all kinds of creases and wrinkles. As for regular, everyday wear, like going to town to run errands, jeans are traditionally worn on the outside of the boots.

Now if you’re the type who doesn’t give a hoot about conventions, then you can throw all that to the wind. In that case, you do you. Because a cowboy doesn’t care what anyone else thinks, anyway, and will wear whatever it is he feels like wearing.

For Women

The same rules don’t necessarily apply to women, though. In fact, the rules don’t apply at all.

Women can wear jeans tucked into boots at any time, and for any reason. The only rule of thumb would be personal preference or issues of general comfort. In fact, not only can women wear boots tucked into jeans in any possible scenario, but women can also wear boots with shorts, leggings, skirts, and dresses. Truth be told, it’s not unheard of to see a bride wearing boots with her wedding gown.

Now that’s not to say that some matches aren’t better than others. A chunky, low-shaft boot is going to look better with boot-cut jeans, and the jeans over the boots, whereas a taller boot, would be a better choice to pair with skinny jeans.

Skinny jeans, or jeggings, or leggings of some sort, are a pair of boots’ best friend. There’s no real need to even tuck anything because the garment actually hugs the legs and their tapered cut allows them to slide right into a pair of boots with ease.

Skinny jeans can be worn with boots of any shaft height. They can even be worn with booties. If you aren’t able to find a pair of skinny jeans to wear with your boots, a pair of boot-cut jeans can be folded neatly to give the same finished look.

To do this, fold a cuff that is about 2 inches tall on the bottom of each pant leg. Pull the extra material together at the back of your calf, neatly fold it over, and then pull a boot sock up over it to hold the folds in place. Then slide your boot right on, and you’ll end up with a neat and tidy look, that’s also comfortable.

Let’s Review

Skinny jeans do pair well with cowboy boots. Any pair of jeans pairs well with cowboy boots. Some cuts of jeans are better suited for tucking into jeans, just as some pairs of boots are better suited for tucking jeans into. That aspect is determined by the size of the leg/leg opening on the jeans along with the space inside the shaft of the boot.

To answer the question. “Should you tuck your jeans into cowboy boots”, the answer for men is sometimes. When you’re working, tuck those babies in. Otherwise, leave the jeans on the outside of the boots.

Note: This is why, for most men’s boots, any fancy designs or exotic materials will be seen on the vamp or the part of the boot that covers the top of the foot because this is the part of the boot that will be visible. You may see brightly colored uppers, but they generally won’t be fancy.

For ladies, the answer is yes if that’s what you feel like doing that day.

Note: Ladies’ boots tend to be much more ornate, with decorations and designs covering the whole boot.

Boots and jeans are a timeless pairing. But if you do ever find yourself unsure about whether or not to tuck your pants into your boots, just remember this: When in doubt, leave ’em out.

Time to go boot shopping!

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About Jerome Glover

Hi! My name is Jerome and I am a writer/editor for GentlemenCenter. I have a passion for helping men improve themselves, and I hope my writing will be able to help you in anything you may need!

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