Classy but Laid-Back: Mens Casual Boots to Wear with Jeans - TV To Talk About | The Tulsa CW

Classy but Laid-Back: Mens Casual Boots to Wear with Jeans


Jeans came onto the clothing scene in the late 1800s when a tailor named Jacob Davis and Levi Strauss & Company got a patent for “fastening pocket-openings.” The patent covered the use of rivets to provide durability for work pants. The rivets worked and denim jeans took off.

Today, jeans are worn as work wear, but if you’re wearing jeans to work, the only nailing you’re likely to be doing is nailing that pitch, project, or awesome line of code. Durability isn’t an issue, but if you want to stand out in the office, you want to pick the right men’s casual boots to wear with jeans.

The basic criteria being you want the footwear to look just as easy and hip as your jeans. Nothing too dressy. Nothing overly casual. Just easy. Like Sunday morning. When you’re wearin’ your 501s, sippin’ Joe and reading the paper. Or maybe you’re just taking your pup for a stroll through the park.

Either way you get the picture. You want to look good in your jeans and boots. So we’ve put together our list of casual boots to wear with jeans that still look classy and work-wearable.

Moto Kicks

Think 60s Beatles boots without the heel and a more rounded toe. Think Italian moto boots. Think Euro zipper boot. Think Pablo.

pablo - men's casual boots with jeans

This boot is hip and stylish, strong and nuanced. It borders on Oxford classy. The leather sole is streamlined.

The top grazes over the ankles and has an easy-to-pull-on tab. It sits tall, flat and fitted, thanks to either a zipper or stretch band.

Color and leather type make it either more classy or more casual. Finished leather in black and the darker browns are for a more refined look. Light brown, tan, or grey-ish suedes are the other end and more casual. But still can look classy and together for work if paired right.

Ankle boots go with jeans. Here’s how.


Black leather gives you more iconic class. These boots are paired ideally with slim cut jeans in a darker color. Think black, dark-grey, or dark-blue denim. Go for black somewhere up top too for balance.

You can also go with a bit wider jean. With both, just cuff them. We like the half-inch single cuff as it lays a bit looser. Full-on double cuffs work too.

Add a jacket, shirt, and tie to elevate the look for work. Try black denim, black turtle, and black long coat. Try a hip tee, preferably black, and blazer to make it sharp.

Or go with an open flannel over the tee instead.

Keep your polished look with regular polish and buffing with leather wax, oil, grease, or balm. It’s easy. And is well worth it.


These are all about class but with a dash of hipness. You know, like an ascot. You know what you want.

Pair with slim-cut jeans or slightly wider and do the half-inch cuff. Again go with dark-blue or black denim. Yes, you can wear brown with black just add in some more brown or blues up top. And our top pick with brown leather boots is brown denim, the darker the better.

Try brown or tan jeans with a crisp white button-down and blue tie for work. Or add a blue jacket if you want to skip the tie to keep it hip and more casual.

Try lighter-brown jeans paired with a dark-brown velvet jacket, grey or tan turtleneck, and grey or tan handkerchief. Handkerchief? You know, folded in your pocket. Sharp!

Go a tad more chill with dark-blue jeans, red flannel, and a yellow vest. Also great is a white tee with an open flannel or dress shirt. Stick with neutrals in the brown shade, reds, or natural greens for the flannel or open button-down.


Pair with slim or a bit fuller jeans with cuffs. Go with browns and blues. You can go lighter with tan. For the top, try pastel button-downs or tees. Or go with the red flannel and a blue vest. A dark brown blazer is a good bet here.

Desert Boots

These ankle boots go to battle for you on the style and function front. In fact, these puppies were worn by British Eighth Army soldiers on the North African front during the Second World War. Their rubber soles flex on varied terrain and their unlined suede uppers let the wind cool your feet as it comes off the hot desert sand.

They also look hot with jeans as you traverse the varied hardwood, concrete, or rug-covered terrain of your office or the streets. They look strong and rugged and still clean up nice, especially if you go with a fresh take, like the suede Declan.

Desert boots are also called chukka boots, by the way.


black leather boots with jeans

The black leather classes it up a lot but the casual cut makes it great with jeans. Like with the moto boots, another ankle boot, pair with black, dark brown, grey, or indigo-blue jeans. Up top stick to a black, grey, or white tee, and a sweater or short jacket. Or pair with fall colors. Think neutrals.

One stellar-and-simple look is raw-denim jeans, a grey tee, and a black sweater.

Straight cut or a bit fuller work well here but everything goes with desert boots. You can even cuff and show some sock.


Again, this casual gets a tad more dressy with the finished leather but the cut keeps it chill. Stick with darker browns and blues for your jeans. With the brown, we give two thumbs up for the sock-showing cuff. Lean fuller straight cut here.

Up top desert boots work well with the same shirts and jackets as with the dark brown finished leather moto boots. Think crisp-white button downs, blue ties, and brown blazers. White tees with the brown blazer are great too.

A blue blazer works too. As does the lighter-brown jeans, brown velvet jacket, tan shirt, and smart handkerchief.

We also vote for dark-blue jeans, red flannel, and a brown vest. Another that passes us with flying colors, er, neutrals is the raw-denim jeans, this time with a white tee and brown sweater.


For more casual boots with jeans, this is your color and material. Pair with a lighter blue or navy jeans. Also, go with darker and lighter browns, but stay away from tan jeans. Too much of the same thing just doesn’t work here.

Cuff these! Pair with navy or red socks. If you’re one for hipster cool, try red and white strips. Blue and gold strips. Or any stripes. Florals and polka dots work, too.

Up top pastels, white, and reds work. Keep it balanced and more neutral if you’re doing the sock cuff.

Try cuffed raw-denim jeans, a white tee, and a jean button-down with rolled up sleeves. Don’t forget the dark brown belt.

Another look that gets our vote? Off-white cable sweater, white tee, darker blue denim, and a black jacket, either light bomber or leather.

Railroad and Work Boots

railroad men's casual leather boots

Think thicker soles, soft rubber. Think towin’ the line building the railroad. Think actually using real nails. Think lace-ups. Think inspired by these things with a fresh style.

These boots are prime casual-jeans material. That you can wear to work too. You know, you can dress it up or down in the office? These give you that I-got-it-covered look.

Keep things skinny without cuff here. Or full and straight or cuffed. Also, keep it neutral or toned down with fall colors, like burnt orange or forest green.

Try black-denim jeans; a black button-down buttoned up and untucked, and a dark green bomber. A long, black top coat is great too. So is a cap. Think baker boy or even a skull cap.

To take it even more casual or outdoorsy, go with a burnt orange pullover and green hooded parka. Pair this with mid-wash or raw-denim jeans, not skinny but straight and a bit full. Then make a big, two-inch cuff.

Literally, this looks great with one big cuff. Swap out the parka for a pullover and you have a full-on vintage vibe happening.

Grab a Pair of Mens Casual Boots to Wear with Jeans

Now that you got the skinny on what’s up with mens casual boots to wear with jeans, you’re in the know and ready to just do this thing. As in, no need to think on this anymore.

Take a look here to find what you need, then order up. We have you covered with all the boots to style-up those jeans for work or street wear. We also have the supplies to keep it all looking tip-top smart.

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