How to Comfortably Wear Hiking Boots with Jeans

When hiking for longer distances, you want to wear your hiking boots. But you also really want to wear your favorite pair of jeans. Is that even a thing or is it just too uncomfortable?

In terms of hiking, jeans just aren’t the best in the world. They’re heavy and tend to rub you in all of the wrong places, especially when your body really starts to heat up. That’s not to mention the chafing and additional weight when they get wet. However, as far as fashion is concerned, that’s a different story. So, how to wear hiking boots with jeans?

You have to go with the right jeans, first of all. This includes purchasing jeans that are boot-cut and the right color to match the hiking boots. For some, it’s fashionable to roll the jeans up at the bottom, rather than pull the lower stitching down over the large ankle section of a hiking boot. 

Color matching is everything too. Most hiking boots have earth tone colors and some, such as the Merrell and Keen brands, look like a cross between sneakers and hiking boots, so they jive with jeans a lot better than others. 

Timberlands are also frequently paired with jeans, as their lighter tan color boots really match well with darker colored jeans. Regardless of what you go with, there are more choices than you think.

What to consider when wearing jeans with hiking boots

man with jeans and boots on standing on a rock
Image credits: James Fitzgerald

There are several things to consider when you’re determined you want to hike in your good ol’ pair of jeans. Keep these 4 things in mind:

  1. Ensure that your jeans are the proper length
  2. Try cuffing your jeans
  3. Tuck your skinny jeans into your boots
  4. Try to avoid regular boot-cut jeans

Let’s take a look at the first thing to consider.

Ensure that your jeans are the proper length

Jeans that are far too short won’t leave you any room for tucking them into your boots which will leave your hiking boots open to wear a nice little red circle of inflammation into your skin. It’ll ultimately aggravate your ankle area, depending on how high the ankle is and drive you crazy.

If you get jeans that are too long and not boot cut, they will tend to bunch up around the top, creating a similar problem. If you end up getting wet from the ankle down, it’ll turn into a virtual nightmare of chafing around your ankles and lower calves.

You really need to get the perfect length in jeans so that you have the option to tuck them in if you want and if you don’t, they aren’t going to crumble up above the ankle of your hiking boots.

Try cuffing your jeans

Cuffing your jeans is another good option with hiking boots, especially if they are too long. All cuffing entails is rolling the bottom of the jeans up to a point where you are comfortable and the cuff remains in place. Sometimes that can be difficult in and of itself, especially if they are far too wide when they are cuffed. 

You can solve that by “pinching” as your cuff them:

  • Grab a corner of fabric at the bottom of your jeans and pinch it together
  • Fold the pinch over to the outside seam, above your outside ankle
  • You only need to pinch as much fabric as you want the wideness of the cuff to be
  • Roll the first roll while maintaining the pinched material
  • Continue to add additional rolls until it is a comfortable height

It’s not the greatest solution in the world but it will do the trick when you need to get your jeans up without the material giving you problems from being too long.

Tuck your skinny jeans into your boots

If you are wearing skinny jeans or you want to wear a pair of skinny jeans with hiking boots, you can simply tuck them into the boot. Be sure to tuck it into the boot over some socks that are high enough to be a good defense between the jeans and boot.

If you’re wearing ankle socks when you use this method, the boots will push your jeans into your skin and create friction as you walk. Of course, that can go from bad to worse in a hurry. So it’s always best to wear some longer socks if you are going to tuck your jeans in.

Try to avoid regular boot-cut jeans

Socks are far more forgiving to the skin than jeans are. Loose-fitting, boot-cut jeans are a good fashionable choice, not a good hiking choice. Going hiking with boot-cut jeans on will cause much of the same problems as allowing the material to bunch up around the top of the boots. 

Except for this time, it will be even heavier at the bottom as you continue to sweat and if you happen to get them wet. Boot-cut, loose-fitting jeans are one of the worst things to wear when hiking that you could choose.

It’s also a haven for every cobweb, acorn, broken twig, leaf, and insect in the entire forest. The area where the boot cut bunches up towards the bottom of the hiking boot will act as a net in the woods, capturing everything that you don’t want to carry around with you. 

It also tends to slide down far enough that it gets caught underneath the heel of the hiking boot, which drags your pants down and ends up tearing your jeans apart at the bottoms. Boot-cut should only be worn in non-hiking activities.

What color jeans should you choose?

Since earth tones are the colors of the day when it comes to hiking boots, it’s pretty difficult to find a pair of jeans that won’t match. Of course, if you take a trip to Walmart in the near future, you’ll find someone making the attempt, if they have shoes on at all. 

There are hiking shoes that are non-earth tones, but you’ll just have to use your best judgment where that is concerned. Traditional blue jeans are pretty much a match for any shade of tan or brown while lighter color jeans go great with dark browns and with very light tans. 

It’s not hard to pick good color combinations when it comes to blue jeans. Even though they simply don’t make the best hiking pants in the world, it doesn’t mean that they don’t go well with hiking shoes at all. 

Jeans for hiking and hiking boots for jeans

Believe it or not, some companies focus much of their time and resources on going against prevailing opinions and trends. That means there are businesses out there who would like nothing more than to prove the anti-jeans hikers wrong, and others who insist that hiking boots can be far more versatile than something to slip on for climbing up and down hills.

For instance, Duer is a retailer that has an entire line of jeans dedicated to hiking. They tend to be a little bit on the stylish side as if they assume that by “hiking,” people are referring to walking fifty yards across a grassy park to set up a picnic.

However, their jeans largely hold up to scrutiny and are far more effective as hiking pants than traditional jeans. Many of them retain denim materials but they are constructed in a much lighter fashion, resisting moisture better and feeling much lighter on the body. 

Then there are the companies who staked their reputation and, their recently unknown names, on making hiking boots and shoes stylish again. Not only did it work, but their brands also exploded onto the scene, becoming some of the most popular hiking wear in the world. 

We’re referencing companies like Merrel and Keen, both of whom manufacture uniquely designed hiking and outdoor boots/shoes that are far more fashionable than anything you would have seen over a decade ago. 

At the turn of the century, someone caught wearing keens might have been laughed out of the building. Now, the Targhee III and the Moab II are two of the most popular hiking boots available on the market. 

Since jeans already go so well with either one, it was only a matter of time before someone came along, put two and two together, and decided to create a new type of jeans that could be worn on a hike. 

That’s not to say that you can’t wear regular jeans on a hike. One major advantage that jeans have over any other type of material is their extreme level of durability. Jeans just won’t quit, even if you want them to quit. 

On light hiking trails, wearing jeans will probably never be a problem. In fact, you can probably get away with hikes around ten miles, so long as you are not going to be passing through any water and getting them soaked. 

Either way, some people will always swear by jeans on a hike, so there’s a good reason for figuring out ways to wear jeans with hiking boots, whether you want to wear them on a hike or whether it’s an issue of fashion and style.

Final thoughts

There’s little doubt that there are ways to modify, put on, or choose the right jeans for a pair of hiking boots. The real question is whether or not you should hike in jeans or just wear them with your hiking boots as a matter of fashion.

The truth may be somewhere in between as new companies are attempting to make “hiking” jeans, while others are insistent that there is nothing wrong with hiking in them. In the end, it all boils down to whatever floats your boat.

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Thomas Godwin

Thomas Godwin is a writer and Marine Corps veteran with a degree in Creative Writing from the Full Sail University. He has been writing content for HeadlessNomad since 2021. Being a veteran, Thomas knows pretty much everything there is to know about the use of paracord, how boots should fit, and nature in general.