I’ve been wearing cowboy boots for over 15 years and in that time I have learned that finding the boots I liked was the easy part. Finding jeans that I liked with those boots was much harder.

Our favorite stores and the internet are flooded with different kinds of men’s jeans but it can be difficult to find out which jeans, and which sizes, work the best for us.

A quick note on men’s jeans sizing

There are a couple of different ways you can determine which size jeans will work the best for you. You can choose your regular inseam (or length) size or you can choose to stack your jeans.

Stacking jeans means wearing a longer inseam size from your true, measured size. For example, my measured size is a 32×34 and when I stack jeans I choose size 32×36.

Stacking jeans has been done historically so that jeans don’t ride up when in the saddle, sitting down or kneeling.

Usually, I like to wear my true size for bootcut jeans and my stack size for cowboy cut or straight leg jeans but it depends on the brand.

Now that you have a good idea about what size might work best for you and what style you’d like to try first, let’s get into the jeans that get the most comments from viewers in my videos and images.

For reference, my height is six feet, one inch, and all of the jeans that follow are my stacked size of 32×36.

Ariat M7 Jeans

There are a couple of different M7 fits from Ariat but the best by far is the Rocker Stretch Legacy Stackable Straight Leg. It’s not too tight around the thighs and it has a slight bootcut opening that works with every kind of cowboy boot there is. This jean has gotten the most compliments in my videos and photos.

Wrangler Retro Slim Straight Jeans

This list would not be complete without the Wrangler Retro Slim Straight jeans. They don’t really live up to the slim fit of other brands and they’re a little roomy in the thighs. There’s also a slight cowboy cut to give you enough room for your boots. Plus they have lots of different colors, my favorite is this Woodburn color. 

Ariat M1 Jeans

Ariat does it again with this more traditional cut jean. Its full name is the Ariat M1 Vintage Stretch Legacy Stackable Straight Leg Jean and it is a classic vintage fit. It’s slightly slim fitting but there’s still room to move and they work with all types of cowboy boots.

Wrangler 20X Competition 02 Jeans

Here’s another Wrangler similar to the Wrangler retro slim straight above but they have a slightly wider leg opening for boots and an Active Flex waistband which makes a huge difference when working and bending over or for big meals! This is another “slim fit” that’s really not that slim fitting.

Cinch Silver Label Jeans

We’re seeing a pattern here, aren’t we? The jeans that get the most comments and love are the slim fit jeans that really aren’t that slim. This Cinch Silver label included! Slim fit jeans get a bad rap for not being roomy enough but this is another great example of a slim fit with a nice amount of room and enough space to fit our boots underneath!

Need more options?

If you’d like to see more options for men’s jeans to go with your cowboys boots, head on over to my YouTube channel where you can find an entire playlist of videos featuring many different styles.