This was an interesting question entered into a Google search and landed on my website, at the tutorial on how cowboy boots and jeans. There is not any information on that tutorial about "problems" that happen when men wear boots.
I am not a podiatrist, and don't even play one on TV, but I have opinions....
To be honest, the most common "problem" is what other people sometimes say, like wisecracks such as "where's your horse?" This happens in areas of the United States where men wearing cowboy boots is not common, such as the Northeast and Mid-Atlantic. Honestly, this is only a "problem" if you allow it to be a problem.
Other problems do occur, namely:
1. Blisters: caused by the boot rubbing on softer skin of the heel and foot. If boots do not fit well, or slide, or are poorly constructed such that threads or interior leather components cause rubbing, then blisters may occur. Solution: a) if you have blisters, do not wear that pair of boots until the blisters heal. b) use moleskin, found at a drugstore, to provide cushion between the tender parts of your feet and the boot. c) thoroughly examine the inside of the boot where the rubbing happened to feel if there are rough parts, and try to remove them or use sandpaper to smooth them out. d) get good quality boots made by reputable manufacturers based in the U.S., Mexico, Canada, and Spain, not cheap Chinese-made junk.
2. Foot pain: usually in my experience foot pain happens when there is not enough support for the arch. Good quality insoles can help. Better quality boots will also help. See above.
3. Toe squeezing: contrary to popular belief, pointed-toe cowboy boots have plenty of room in the foot at the toes for human toes to fit. However, there have been reports about toes being squeezed together too tightly in some cowboy boots. Solutions: a) get pointed-toe cowboy boots a half-size larger so they are longer in the toe, or b) get boots that have a rounded toe so there is more room in the toe box.
4. Trips and falls: some people are not accustomed to wearing boots that have higher heels than typical dress shoes or sneakers. It is not unusual for a guy new to wearing boots to strike the boot's heel on a stair or sidewalk and fall down. Solutions: a) practice walking in your boots on a smooth surface. Seriously -- practice indeed helps! b) lift your feet rather than glide along. c) get boots with "walking heels" rather than higher, underslung heels. Most men don't take well to high heels, myself included.
5. Wearing cowboy boots for the wrong application or at the wrong time: most cowboy boots have smooth leather soles. Because of that, the boots have little traction. If pavement is wet -- or worse, if pavement is icy -- then it is very likely that you could slip and fall. I do not recommend wearing cowboy boots on wet, icy, or snow-covered pavement. Doing so is a recipe for disaster, IMHO. Further, if you operate a motorcycle, I do not recommend wearing cowboy boots with smooth leather soles, either. Again, it is a traction issue. If you like the cowboy boot design and wish to wear boots of that design while operating a motorcycle, at least get them with rubber soles. If you have a pair of cowboy boots with leather soles that you would like to use on a motorcycle, then bring the boots to a cobbler to have rubber soles (or at a minimum a sole and heel plate) applied.
I think these are all of the common problems when wearing cowboy boots that I can think of. If you have more, please comment. That way, other people will see your comments when they read this post, or find it later which happens often thanks to search engines.
Life is short: wear boots!
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