An Excerpt of the History of Cowboy Clothing from Darla Sue Dollman at Wild West History
"Although current styles keep the pant leg outside of the boots, cowboys in the 1800s wore their pant legs tucked inside so they wouldn't snag on twigs and thorns. (If you haven't figured this out yet from these detailed descriptions of cowboy attire, cows have a habit of wandering into thorny areas where they are...rescued by cowboys!)
Cowboys spent as much as a month's wages to have their boots custom made. The only cowboys who wore ready made boots were either inexperienced green horns or cowboys saving their money for the real thing!
Although one might think a bandanna would be used for show, this is far from the truth. Bandannas came in a variety of bright colors to make the cowboy more visible in bad weather. They served--and still serve--many purposes. They block the hot Southwestern sun to prevent sunburn and mop up sweat from the brow. They keep the dust out of the mouth and nose during dust storms and warm the ears in cold weather. They are also used as washcloths, tourniquets, and blindfolds to lead horses out of burning barns.
Finally, the cowboy hat. Cowboy hats shield the top of the head from the heat of the sun, and the eyes from the sun's glare. The keep rain off the face. They can be used to wave to a friend from a distance, and to smack a slow horse on the rump.
Nowadays, cowboys where hats according to what suits their fancy. In the 1800s, style choice depended on region. In the Southwest, cowboy hats had tall crowns and wide brims. In the North, brims were narrow and crowns lower so they would not blow away. It was easy to identify where a cowboy came from by the style of his hat."