Men’s Style Guide: Cowboy Boots and Jeans

Both cowboy boots and jeans have evolved to include a wide array of cuts, designs, washes, and colours. From dress boots to work boots, straight-leg jeans to boot-cut, there’s a lot to choose from. But finding the right combination of cowboy boots and jeans is as easy as understanding a few style rules and tapping into your own personal preferences.

How to Wear Cowboy Boots With Jeans

How do you wear cowboy boots with jeans? As a general rule of thumb, we recommend wearing medium to dark-wash jeans over your boots (not tucked in). The jeans should be fairly form-fitting in the upper legs but have enough space in the lower leg to accommodate the boot, without showing an outline. In the sections below, we’ll talk about how to find the right length, cut, and colour.

Cowboy Boots and Jeans: Finding the Right Length

When choosing a pair of jeans to wear with your cowboy boots, it’s important to find the right fit. The jeans should be long enough to protect your legs and cover the shaft of the boots, but not so long that they drag in the back or get stuck under your heel. Ideally, they should rest just above the heel of your cowboy boots by a quarter to a half inch. If you want to wear shorter jeans to show off your footwear, have the hem rest right above the instep of your cowboy boots.

The Best Jean Cuts for Cowboy Boots

When talking about how to wear cowboy boots with jeans, you can’t overlook the cut. The best jean cuts to wear with your cowboy boots are:

• Boot-Cut - Boot-cut jeans and cowboy boots go together like peanut butter and jelly. The flared leg accommodates your boots without bunching around your legs.
• Regular/Straight Leg - Regular and straight-leg jeans work fine with cowboy boots, but you might have a little trouble putting on your boots, since you’ll have to roll up your jeans to get them on, then roll the jeans back over the boots.
• Relaxed Fit - Relaxed-fit jeans are okay to wear with cowboy boots, but you might want to consider a shorter inseam to compensate for the extra bagginess.

Jean cuts narrower than a straight leg probably won’t fit over your cowboy boots, meaning you’ll have to tuck them (not advised unless you’re doing some heavy-duty work).

The Best Denim Colour for Cowboy Boots and Jeans

These days, people are wearing nearly every colour of denim with their cowboy boots. But generally speaking, the best colour for a modern look is a dark blue or charcoal wash. Medium blue jeans are perfect for daytime wear, and darker washes are great for nights out. Light-wash jeans with cowboy boots have largely fallen out of fashion, but if you want to recreate a retro look, they could be the piece that pulls it all together.

Ultimately, your choice on how to wear cowboy boots and jeans comes down to personal preference, but with this little bit of knowledge on proper length, cut, and recommended colours, you’ll have an even better starting point.