In the beginning, shortly after cowboy boots had been designed and were being sold to riders on the cattle trails, the life of a pair of cowboy boots was pretty predictable. Many nights of their lives would be spend on the trail, with weeks passing between seeing civilization of any sort. These boots faced many challenges from the environment. They forded rivers, they protected legs from rocks and brush and sometimes even wildlife, such as snakes. They spent most of their time in the stirrup and they were as rough and tumble as the men wearing them. These were boots designed for the job, too. They had thick leather shafts, stitching on the outside so as to not irritate the skin when worn constantly, stacked heels and pointed toes for an easier time with stirrups and so on. If you were wearing western apparel and cowboy boots, you likely spent a fair time around cows, which is obviously how the name cowboy developed. However, cowboy boots have had continued popularity with those that are working in the same environments, even if they don't spend the majority of their time in the saddle, just because cowboy boots and western wear is the best functional, strong, and durable clothing that was designed for those elements.
Today, the lives of western wear boots are a little more varied, and are seen beyond western communities. You still have those who will spend a majority of their time around cattle. However, you also have boots that will spend their life on the rodeo circuit. Another style of boot, a spin-off from the original pattern of cowboy boots, are roper boots that are a special design for ropers who need to be quick out of their saddle and able to hit the ground running during competitions. However, these are not the only people that purchase cowboy boots and western wear. Other cowboy boots are purchased by those who are simply interested in them for the aesthetics. These cowboy boots might be worn in the city, they might go out dancing, and will likely be mixed and matched with clothing from all different styles. The accessibility and availability of cowboy boots to anybody who wants them is a product of both their popularity as footwear (for function and fashion) and the imagery they evoke.
One of the reasons that cowboy boots and western wear seems to be so timeless is that the movie industry has re-imagined the wild west many times, with different themes. There have been many influences on the western film genre. There are more politically correct renderings that show women and Native Americans in a different light than earlier films did. There have been samurai westerns, spaghetti westerns and even steam-punk westerns. The more westerns are re-invented and re-vamped, the more likely it is that western apparel will remain current, popular, and fresh. After all, much of society takes note when Hollywood speaks, even if they don't necessarily intend on copying Hollywood, it seems to happen very naturally.
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Western apparel and cowboy boots are functional and the norm for those that still work western occupations, but cowboy boots and western wear is not isolated to these communities. It's popularity spins off into fashion as well, thanks in part to Hollywood's western genre (and all the sub-categories that have developed since). This has led to varying times of popularity in mainstream fashion. Thanks to online retailers, like the Boot Store, that have a wide selection that ensures everyone will find western wear that fits their function or fashion needs.