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Best Cowboy Boots: A Guide for Looking Sharp in the Saddle

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Cowboy boots have become an iconic part of American culture, conjuring images of the Wild West and country music stars. While often associated with cowboy culture and rodeos, cowboy boots have also become a mainstream fashion staple that offers both style and functionality.

In this comprehensive guide, we’ll cover everything you need to know about finding and wearing the perfect pair of men’s cowboy boots, from types and critical features to styling tips.

What Makes Cowboy Boots So Special?

Cowboy boots stand out for their distinctive style and design geared towards horse riding and ranch work. 

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Key features like a tall leather shaft, angled cowboy heels, and pointed toes evolved as practical elements to protect cowboy’s feet and provide stability in the stirrups.

Beyond functionality, cowboy boots incorporate decorative stitching patterns and exotic materials like exotic animal hides that convey a rugged, adventurous vibe. When you put on a pair of cowboy boots, you can’t help but channel the independent spirit of the American cowboy.

The 2 Main Types of Men’s Cowboy Boots

There are two main types of cowboy boots for men:


Western Boots

The cowboy boots most people visualize, Western boots feature fancy stitching and exotic materials with a taller shaft reaching mid-calf. Western boots have high-angled heels designed to prevent sliding in stirrups and pointed toes to slide in and out quickly. Favorite Western boot embellishments include decorative stitching and ostrich, alligator, lizard, and other exotic hides.

Roper Boots

Roper boots have a lower, shorter shaft reaching just above the ankle bone and feature basic leather with minimal ornamentation. The heel on roper boots is also less pronounced than on Western boots. Roper boots are the more practical, helpful choice worn initially by ranchers and cowboys working cattle.

Tecovas has quickly become one of the most popular cowboy boot brands on the market. Founded in 2015 and based in Austin, Texas, Tecovas aims to provide handmade boots combining traditional Western styles with modern comfort at reasonable prices.


Tecovas offers classic men’s Western boots in calfskin and exotic hides like ostrich and alligator. Customers praise the quality materials and construction along with comfort elements like cushioned insoles. With free shipping and returns, you can try out Tecovas risk-free.

Breaking in Your Cowboy Boots

Many first-time cowboy boot shoppers wonder: 

Are cowboy boots hard or uncomfortable to break in? The reality is breaking in cowboy boots requires some patience for most people. Expect some blisters and soreness early on.

The tall leather shaft needs to soften and conform to your legs. Rubbing alcohol helps soften the leather quickly. Wear your cowboy boots with thick socks around the house to gradually stretch them. The iconic cowboy heels shift your foot position and stride, which takes an adjustment period to get accustomed to initially.

Though breaking in cowboy boots can be painful, adequately sized, and fitted, high-quality cowboy boots feel amazingly comfortable and custom-tailored. Investing in good cowboy boots means years of comfortable wear after pushing through the first few weeks.

Are Cowboy Boots Warm for Colder Weather?

Cowboy boots excel as winter footwear thanks to their high shafts and closed-toe box. 

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The tall height keeps snow or rain from getting inside the boot while encasing your feet tightly to prevent heat loss.

For even warmer cowboy boots, styles with a sheepskin or faux fur lining offer ultimate warmth and coziness for trucking through snowdrifts or frigid days on horseback. Insulated options are also available for extreme cold.

Pair your winter cowboy boots with thick wool socks, and your feet will stay nice and toasty warm all day long without the bulk of snow boots.

Best Jeans to Wear with Cowboy Boots

What tops to wear cowboy boots with? These are commonly asked questions most guys have when starting to wear cowboy boots.

The best pants to pair with cowboy boots are jeans – either dark rinse or raw denim blue jeans with a straight or slim cut. Other great bottom pairings include canvas pants or chinos in tan, olive green, brown, or black.

Cowboy boot outfits work best with straight or relaxed jeans that comfortably fit over the shaft. Bootcut jeans are also made to sit over cowboy boots perfectly. Avoid skinny jeans or pants since they’ll be challenging to tug over the taller shafts.

Complete Outfits For Styling Men’s Cowboy Boot

Now that we covered individual pieces let’s look at some classic ways to style your cowboy boot:

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Western Wear Outfits

  • Cowboy boot with jeans and a button-down or plain white T-shirt channel effortless cowboy cool. Throw on a leather jacket or jean jacket to complete the Western outfit.

Country Casual Looks

  • For a bright, casual vibe, try brown or black cowboy boot with chinos and an Oxford shirt or polo. Swap the polo for a crewneck sweater in autumn.

Formal Cowboy Boot Outfits

  • Daring gentlemen can rock black cowboy boot with a suit for events like weddings, night outs, or date occasions. Choose proper or short cowboy boot with slim-fitting suits in navy, gray, or black.

Rugged Looks

  • Play up the ruggedness of cowboy boot with canvas pants, denim jackets, and flannel shirts for weekend camping trips or a night concert.

Additional Cowboy Boot Styling Tips

  • Match leather shades – Brown boots work best with brown pants and black boots for black bottoms.
  • Contrast textures – Leather cowboy boot with cotton twill pants or shirts
  • Show off details – Tuck pants over shafts to display ornate stitching.
  • Cuff wider pants – Cuff wide-leg pants help slenderize bulky silhouette.

Finding Your Perfect Fit

Fit makes all the difference between comfortable cowboy boot you’ll love wearing and painful boot languishing in your closet.

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Key Elements of Proper Cowboy Boot Fit
  • Snug but not tight through heel and arch
  • There is enough room to wiggle toes.
  • Deep and wide enough through the ball of the foot
  • Half-inch space from the top of the foot to the boot ceiling

Well-fitted cowboy boot feel like a firm handshake around your foot. The leather will stretch and soften over time, so resist the urge to size up. Half sizes and different widths are available to dial in the perfect cowboy boot fit.

Are Cowboy Boots Comfortable?

This depends on the style. Cowboy work boot designed for riding tend to run narrow and stiff. Fashion cowboy boot focus more on comfort with cushioned insoles, flexible soles and soft leather.

Brands like Tecovas use comfort technology to make cowboys feel like slippers after the break-in period. So, for easy-wearing cowboy boot, opt for fashion over function.


What shirts go well with men’s cowboy boot?

Western-style button downs, henley shirts, polo shirts, t-shirts, and flannel shirts pair nicely with men’s cowboy boot. Pick colors and patterns like white, black, gray, brown, navy or red plaid for easy pairing.

What pants should you wear with cowboy boot?

The best pants to wear with cowboy boot are straight leg, bootcut, or relaxed fit jeans in darker washes. You can also wear canvas pants, chinos, or corduroys in colors like tan, brown, olive green, or black.

Do cowboy boot make your calves look bigger?

The shaft circumference of cowboy boot can accentuate calf width, especially for skinny legs. opt for narrow shaft diameters and wear straight or slim jeans to balance proportions.

What socks should you wear with cowboy boot?

Mid-calf height cotton boot socks allowing feet to slide in easily work best. For added warmth and friction reduction, try performance wool boot socks.

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