How to Wear Cowboy Boots

Last Updated: January 31, 2023 References

Cowboy boots are a staple of American fashion and always make a statement. Ranch hands, country singers, and famous Western stars have made them a classic look: distinctive, rugged, and slightly edgy. Cowboy boots, worn with flair and balanced with well-structured, stylish pieces, can set most outfits to good advantage.

Part 1

Part 1 of 3:

Wearing Cowboy Boots for Style

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Embrace the boot. If worn well, cowboy boots can be a fashion statement for both men and women. Why not embrace them? Cowboy boots have a long and storied past: think cowhands, ranchers, John Wayne, and Clint Eastwood. They can be manly for men, stylish for ladies, and a great addition to a wardrobe.
- The height, tapered toes, and decorations make cowboy boots distinctive. They will be a focal point for your outfit.
- The cowboy boot's tapered toes are a fun contrast to the usual dress shoes. The added height provided by the heels will also create the illusion of being taller.^{[1]
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- Plain cowboy boots are a rarity. Most stand out with a variety of colors, leathers, and finishes, and many have added tooling or stitching.
2
Know the different styles of cowboy boots. There are several basic kinds of cowboy boots out there, each with their own look. From the classic model to Ropers and Buckaroos, there is a style out there for everyone. Learn more about these and pick one that suits you and your personality.^{[2]
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- The classic boot usually has a shaft about 12 inches high and a Cuban-style heel, meaning that it is angled inward. In the old days, this design fit right into your stirrup.
- Ropers are designed for rodeos and have a lower shaft. The toe is also more rounded and the heel more like that of a typical work boot.
- The Stockman is a lot like the classic look. However, it has a shorter and wider heel.
- Western work boots tend to look more like the Roper, but with a larger (and sometimes steel) toe. Many will also have rubber soles for better traction.
- Buckaroos may be the most flashy of all. They are tall – over 14 inches – and often have detailed tooling or decoration on the shaft. They are made to protect the legs, and to be seen.
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Choose the right size. In addition to your shoe size, the boots need to be the right width. Women's cowboy boots are typically sized in A, B and C widths, while men's cowboy boots are typically sized in B, D and EE widths.
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Be confident. The key to wearing cowboy boots well is to have confidence. In most areas, cowboy boots are uncommon and maybe even a bit gauche. People will look. You have to wear them like you mean it and carry yourself with flair.
- Mind your body language when you walk: backbone up and chest held high. Your posture and demeanor will show if you're self-conscious.
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Try to avoid camp. While you should be confident, be careful not to take things too far in the direction of campiness. The cowboy boot, used poorly, can look slightly ridiculous – think the Village People or Marty McFly in Back to the Future III. Use your better judgement; the key is subtlety.^{[3]
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- Try not to incorporate more than one “Western” themed item into your outfit at once, for example, unless you're actually working on the range. If you're wearing cowboy boots, avoid spurs, cowboy hats, ponchos, and bolo ties.
- Boots with garish colors, too much decoration, or exotic skins like shark, skate, or snake will also draw extra attention.

Part 2

Part 2 of 3:

Sporting Boots for Guys

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Don't tuck jeans into the boot. Some styles like Buckaroo boots are elaborately embellished, and you may want to wear it so that the decorations are seen. But for guys, the best style is to wear jeans over the boots, unless, that is, you're actually doing work on horseback.^{[4]
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- Favor boot-cut jeans that are dark and close-fitting. You'll want your pants to accentuate the boots as best they can. Avoid normal, work-style jeans.
- The front of the boots will still be visible – there won't be any question that you're still sporting footwear with a Western flair.
2
Stick with classic washes. Medium and dark wash jeans are usually the most versatile jeans to wear with cowboy boots. However, black, beige, or brown jeans can also work well as long as they match the boots in color.
- Light blue washes have a tendency to look a little outdated. Avoid acid washes, as well.
- The same goes for some of the brighter colors now in fashion, i.e. yellow, white, green, or pink.
3
Gussy things up with dark trousers or a casual suit. Aim for a more put together look by switching your jeans for chinos or twill pants. That said, beware mixing boots with the overly formal. Unless you are in Texas or Oklahoma, you might get strange looks for combining cowboy boots with business wear.^{[5]
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Research source} Brown, black, or black cherry colored pants can work well.
- Well polished boots go particularly well with trousers.
- You might even be able to pull off khakis in a traditional brown, tan, or cognac color.
- If you opt for trousers over jeans, be sure that there is enough room in the pant legs and avoid unsightly bulges.
- In some areas, it is acceptable to wear a so-called “Western tuxedo” for formal events. This features a cowboy hat and boots with a normal black-tie tux. Just be sure your boots are black and highly polished.
4
Be sure your pants are sufficiently long. When wearing cowboy boots, your pants should come down to the foot of the boot or a little longer. They should not be long enough to drag on the floor, however, or too short.
- Keep in mind that most cowboy boots have a taller heel than regular shoes, as much as one or even two inches. As such, your usual jeans may not be long enough.
- Look for jeans that “stack.” This refers to the soft fold that forms in the jean when it extends past the foot of the boot.
- The stack is a stylistic preference, but it will give you a slightly rugged appearance and is preferred by many men.

Part 3

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Styling Boots for Women

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Pick your favorite material and color. Cowhide boots are classic, and the most classic hues are brown and black. You can also find women's cowboy boots in other colors like white and red. Leather boots can look casual or classy, depending on their condition and what you pair them with. You could also wear suede boots, which are a little more elegant but harder to maintain.^{[6]
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- Pay attention to the style and shape of the boots. A calf-length cowboy boot with a pointed toe is a classic style. But nowadays you can find ladies' cowboy boots in shorter lengths or with rounded or square toes.
- Be aware of that there are other materials than just cowhide, like quilled ostrich, caiman, crocodile, and snakeskin.
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Wear cowboy boots over tapered jeans. Skinny jeans hug your leg and have little, if any, extra material. As a result, trying to stuff your boots under them will only make your legs look bulky and frumpy. Wear your cowboy boots over the jeans for best results.^{[7]
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- This look works especially well when the skinny jean and country boot are balanced out by a chic city jacket or blazer.
3
Sport boots with leggings and tights, as well. This is another way to show your boots to the world. If you have a long shirt, sweater, skirt, or dress, you can wear leggings or tights under your boots to keep your legs covered during chillier weather.^{[8]
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- Try wearing your boots with leggings and a tunic dress or cardigan, as well.
- You can also match them with bright tights and a dress or tunic for a unique look.
4
Replace high-heels with boots worn under your jeans. The height of the classic cowboy boot mimics that of a normal pair of heels, and the front looks like the front of a casual yet chic closed-toe heel. Try this look out by wearing the jeans over the boot.^{[9]
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- When wearing jeans or other pants over your cowboy boots, it's best to go with a boot-cut or flared style.
- You should also opt for longer jeans that will cover almost all of the boot to the toe. The heel will add one or two inches to your inseam.^{[10]
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Wear the boots with a dress for a feminine look. Loose-flowing, airy dresses can create an interesting contrast with the structured, rugged look of a cowboy boot. Pick a dress that stops at or slightly above the knee to show off more of the boots.
- You can also try your boots with a classic dress. A little black dress paired with black or sheer tights and black cowboy boots can look surprisingly sleek and stylish.
- Wearing your boots with a dress in a simple, structured cut is a good way to give an otherwise elegant piece a playful twist.
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Keep your outfit fairly simple. Regardless of its cut, pattern, and color, keep your clothing relatively plain. Cowboy boots are a statement piece, especially when worn in a way that allows the full boot to be seen. Wearing the boots with a garish print will only cause your outfit to look busy and loud.^{[11]
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- Don't feel the need to banish embellishment entirely. For instance, brown boots can go well with patterned dresses.
- At the same time, the most important thing is to let the boots be the focus of your outfit.
- Don't wear your boots every day. Save them for special occasions for maximum impact.

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Is it OK to wear skinny jeans with cowboy boots?

Kathi Burns, CPO®
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Kathi Burns is a board certified Professional Organizer (CPO) and Founder of Organized and Energized!, her consulting business with a mission to empower people to master their environment and personal image by assisting them in taking control, making change and organizing their lives. Kathi has over 17 years of organizing experience and her work has been featured on Better Homes and Gardens, NBC News, Good Morning America, and Entrepreneur. She has a BS in Communication from Ohio University.

Kathi Burns, CPO®

Image Consultant

Expert Answer

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If you're wearing boots, opt for either bootcut or skinny-leg jeans. Bootcut jeans will fit easily over the boots, while you can tuck skinny jeans in nicely inside the boot. Straight-leg jeans, however, won't fit over the boot, and they'll bunch up if you put them inside of your boots.