One might think, "why does anyone want to know how to put on cowboy boots. I mean, you just sit down and pull them on, right?"
Yep, that's right. However...
... not everyone can pull on cowboy boots all that easily. Recently, I received an email from a guy who is not accustomed to wearing boots. He bought a pair of boots via a reputable on-line merchant. He even got instructions on how to measure himself for boots before he placed the order. Trouble is, the vast majority of internet boot retailers only give instructions on how to measure the foot, not the calf.
The guy who wrote to me said that he received the boots, took them out of the box, pointed his toe into the boot and pulled ... and pulled ... and pulled, and the boot wouldn't come on. He further described that the boot shaft (calf circumference) was too narrow.
He wrote to me for advice on what to do. Short story: I suggested that he return the boots and go with another brand, or better yet: custom boots made to his specific measurements.
The guy contacted some others for advice, and someone told him to use plastic grocery bags on each foot. Put his foot in a bag, then into the boots, then pull on. Well, that works for a few people, but only to get the boot on the leg. But the bag doesn't just pull out once you get the boot on. So what do you have? Roasted ankle and foot! The plastic will not allow natural body heat to dissipate, nor sweat evaporate. Soon enough, your foot begins to heat up, sweat, and then ... da da da dum ... swell. Uh-oh! You could barely get the boot on, and now you're foot is hot, sweaty, and swollen, so you won't be able to pry the boot off with a crowbar! This is NOT a good idea! Don't believe that old folklore. It doesn't work!
If the shaft is slightly narrow -- that is, you can get the boot on but it is a tight squeeze -- then it may be possible for a cobbler to stretch the boot shafts for you to accommodate your leg. But most boots can only be stretched at most 3/8 of an inch. Sometimes that can help, but most often, it's not enough.
Some cheap boots have narrower shafts that higher-quality boots. Check the manufacturer. I have found that Dan Post, some Tony Lama, some Justin, Nocona, Lucchese, and a few others have a slightly wider instep and calf, which are more forgiving to guys with muscular (or large) calves. Word of warning: if the boots cost less than US$140, expect narrow shafts and other manufacturing short-cuts which is why they are cheap, but also may result in the boots not fitting properly.
The best bet, overall, is not to give up on wearing cowboy boots, but rather, have them made custom to fit you. I like Champion Attitude Boots for the wide assortment on styles of boots as well as having some boots that are affordable (they also make some that are very expensive. Plain and simple boots do not cost an arm-and-a-leg.)
Alternatively, try regular harness boots. While it may seem that the harness strap would make the instep tight, it does not. Harness boots generally have a wider instep and calf circumference, so that style of boot may fit you, while traditional 13" cowboy boots would not.
It is best if you can go to a western store, or even a well-stocked motorcycle store, and try on a pair or two of different styles of boots. That's really the only way to know if the boots will fit.
Life is short: wear boots!
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