Sharp and Rugged: The Perfect Suit and Cowboy Boot Combo

If you’ve spent even a little time in the South, you’ll know that Texas cowboy boots paired with a suit can be a suave and sophisticated—if not more unusual—look all unto itself. Boots with a suit can make an interesting statement, and the flashy fashionability of the cowboy look can elevate that in just the right way—when worn well. 

That’s why you have the Oliver Wicks team, of course! Today, we will walk you through wearing this niche look the right way, with elegance and style.

Cowboy Boots and Suit Combo

Think for a moment about where you’ve seen a suit with cowboy boots before. It’s a staple for law enforcement and mega-church preachers, and has even been spotted on a President or two! Provided it’s suitable to the overall ambiance of the function, cowboy boots can lend you a fierce, authoritative, and confident air that’s hard to beat.

It does pay to ‘read the room’ before making this fashion choice, however. While in the right environment it can even be work-appropriate, for example, in business-casual environments, you need to know you’re making a solid fashion choice before choosing it. Of course, if you reside in a Southern state, you can wear it almost anywhere, including the boardroom! 

Cowboy boots make an interesting choice for smart casual with a difference. They can also be a supremely lovely choice for weddings, provided they’re not black tie dress codes. And they are very practical at outdoor events of all sorts.

If you’re going to choose this trend, it’s best to lean into it. While not everyone will feel comfortable in a bolo or cowboy hat, it does finish the look beautifully—and is great for outdoor warm weather events where you don’t want to catch the sun. This may also be the rare occasion where a (somewhat) flashy engraved belt or larger buckle should come out of the wardrobe to play.

What Type of Cowboy Boots to Wear with Suits?

If you want to wear cowboy boots with a suit, there’s one firm rule to follow: If it would actually work on a ranch hand, don’t wear it! Hard-toed caps, thick rubber soles, and other utilitarian features will instantly clash with the smooth sophistication of your suit. 

Go for leather soles and sophisticated ‘dress’ cowboy boots instead. Classic roping, walking, and riding styles will all work, with subtle differences in the toe box and height you can choose to suit yourself. While square-toed cowboy boots are in at the moment, they also look workaday and low-tier, so you’re better off with a pointed or subtle almond toe with a suit. 

Exotic or worked leather can make a statement but use it sparingly and in line with the rest of your look. Let the boots be the statement part of your look. Your boots should be sleek and polished, so avoid suedes and rugged/distressed leather with a suit—save them for jeans instead. It’s too much of a mood clash. Instead, invest in quality shoes that will look great for years to come.

A lot of the stand-out design features of cowboy boots are up the shaft of the boot, so you don’t want to obscure them completely. Below, we’ve looked at how to match your pants to your boots.

What Suits to Wear With Cowboy Boots?

You can carry both a three-piece and two-piece suit with cowboy boots, though two-piece suits are more common right now. Choosing the right length and type of suit pants for your cowboy boots is critical. As with all pants, the tip of the hem should brush the ‘vamp’, or ‘foot’ part of the boot. But it absolutely shouldn’t pool there in any way—you want to show off the beauty of the shaft design. 

You may need to have a tailor take up the pants on your suit a little to make them work with these unique boots. While a fitted taper can help draw attention to your boots, you don’t want your pants so tight that they leave the impression of the boots from the inside—that just looks like your suit doesn’t fit! 

A looser ‘modern’ cut is best here. Remember the Oliver Wicks motto, you need—the fit that suits you (and your cowboy boots)!

Cowboy Boots and Suit Color Coordination

As with most leather shoes, black or brown are the go-to for this style. For once, brown really shines as the ‘traditional’ cowboy boot color, too, so if you’re looking for an interesting way to pep up a classic gray suit, look no further.

Monochrome suits, like gray and black, will heavily favor black leather, although brown will pass with lighter and middle grays. The warmer tones of navy are ideal for carrying the classic brown. If carefully chosen to match hues, you can even make a tan or camel suit work for this look. You could also make a real statement with dark brown leather and a burgundy or dark green suit, or something adventurous like plum and dark brown. But navy and charcoal/gray remain the best choices to play with this aesthetic.

Overall, you’ll see dark brown boots as the most popular color combination, especially with blue suits, and while it’s hard to go wrong with leather, make sure your overall look is sleek and well-matched in tone—warm browns for warm colors, cooler browns for cooler colors, and black for the monochromes.

What to Avoid With Cowboy Boots

As with all men’s boot styles, the worst thing you can do is tuck your pants into your boots. We do want to show them off, but you don’t want to look childish or like you’re wearing a costume piece.

That same advice goes for the rest of your look. We’ve already seen how a few other ‘cowboy’ touches can pull the look together, but make sure you're not venturing into caricature territory. It’s a style, not a costume. Keep the other nods to Western looks subtle and elegant, not bold and attention-seeking. 

Denim on denim is best avoided—even a denim-colored suit may be too much, regardless of the high-end wool that made it! And shorts, tuxedos, and ‘skinny’ or ‘spray-on’ pants (even jeans) are off the table completely. Please don’t make us tell you why!

There’s a more subtle consideration, too—your comfort! Leather boots and shoes are a fantastic investment, but they do need to be properly ‘broken in’ to wear well. Limping through a wedding (especially if it's yours) or a work day because your boots gave you blisters will make you look gauche. So, try them out for a good few hours at home before you wear them ‘live’ and choose comfortable, breathable socks that pad you well.

Conclusion

Cowboy boots have escaped the South and become a trendy, fun way to pep up smart-casual and casual looks. With plenty of visual interest and quality leather to back them, they make for a great way to experiment with the boots and suit look in an intriguing way. 

If you love to keep your suit wardrobe on-trend and interesting, our Oliver Wicks newsletter is packed with tips and tricks like this—you can sign up from any page on our website and get them delivered right to your inbox. And you are always welcome to reach out to us at custom@oliverwicks.com if you need any specific help in choosing the perfect custom suit for your new look, too!