First: Any native Texan can tell you that cowboy boots evolved back in the wild wild west as a practical form of footwear for riding the range. They had a tall, thick leather shaft (the part that goes up your leg) to protect your ankles and lower legs, when riding horses, from mesquite trees (which have thorns) and various other brush out there on the range with stickers and scraggly branches. (English riding boots do the same but are not as tough or thick.) Riders know that horses love to try to brush the inexperienced rider off by gliding through a thorn bush and hoping it makes the rider miserable or throws him off completely. Old cowboy boots are more utilitarian than decorative, and only came in two colors: dark brown or black. Even today, no self respecting man would ever be caught dead in any other color. Both girls and guys have every day/utilitarian models, and dress models. Girls can get away with wild colors for dress boots, but men need to stick to dark brown or black. (I made hubster, a Yankee, get rid of a pair some well-meaning but clueless family member bought him when he moved here because they were a light brown, almost beige color. Homo! And not even good homo. A gay man, being fashionable, would not have worn them. Even Carson on "QE4TSG" would advise against them.) That's why you truly want to steer clear of anything you find on a "sale" rack......that just means no one else wanted them. There's a reason! Notice the shaft is fairly wide, to accommodate muscled legs to fit in to them.
You can do a search on the internet for old cowboy photos, the history of cowboys, etc and turn up a variety of pictures from this era, some with the boots worn inside/under the pants leg, some worn with the pants leg tucked in. (To tuck or not to tuck the pants material into the boot is a matter of personal preference, and often depends on circumstance. Sometimes you are protecting the fabric of your pants, sometimes you are protecting the boot. Depends on what you are doing. Generally speaking, it is OK to tuck the pants fabric into the boot while riding the range, but an affectation to do so in town. People will laugh at you if you are a man and walk around in the city with your pants leg tucked in to your boot like a Cossack or in the style of English riding boots. There's a reason cowboy jeans are flared! To fit over your boots! Girls can sometimes get away with it if they are cute, and their whole ensemble is "cowboy chic".) Because these boots evolved initially for riding horses, they had a pointy toe (easier to get into the stirrup in a hurry) and a 2-3 inch heel that was slanted or cantilevered under (helped you hook your heel, and keep it, into the stirrup, and did not bruise your horse's ribs). An old pair of boots, well worn and loved, will show wear marks on the toes and the heels, from actual use as originally intended. Thick leather soles could be replaced if that part of the boot wore out before the top did. The loops and holes at the top are designed for you to put your fingers in and pull them on. Utilitarian, all around.
A new pair of cowboy boots, like many kinds of boots, will be stiff when you first put them on but mold to your feet and soften up some as you wear them. They should be comfortable, however, from the beginning, because if they don't fit you just right, they never will. The best thing to do is to try on different pairs/brands, and find one that works for the shape of your foot. (I have an unusually high arch, and have to select shoes/boots that accommodate it. Hubster has wide feet, like a hobbit.) You don't want them to pinch , rub, or for your heel to slip while trying them on in a store.You definitely wear socks, crew or knee-high, with boots.
Looking at archives of old cowboy photos, you can tell a lot about the person in the photo from the boots on his /her feet. Dusty banged-up boots reveal someone who truly worked in them, and maybe could not afford a second pair. Fancy showy boots, with the pants leg hiked up so you can see them, reveal a dandy. In many old photos, I noticed, the cowboy has on a soft moccasin type boot with fringe around the top of the shaft, which brings me to my next point: wearing cowboy boots, as they were originally styled, all day in the city on concrete and other hard surfaces, isn't really that comfortable. Wearing them indoors with spurs attached was a no-no. That's why cowboy boots evolved into what are called ropers. (Originally after the brand that invented them, but now applied to all items in that category, much as Southerners call any soda pop or soft drink "coke".)
Contrast those real life cowboy looks with the cowboy chic wanna-be's: these folk turn up in C&W bars in Austin or Dallas, or at fancy resorts in Colorado, Arizona, Montana, New Mexico, often apres ski, strolling around restaurants and bars, shopping. They are wealthy city folk who indulge a fantasy of being a cowboy/cowgirl while on vacation, and they shop at tres expensive boutiques that sell trendy expensive western-themed fashion ensembles. This is where folk buy and wear the truly crazy patterns/styles/colors of (lately, retro styled with pointy curved toes and distressed to appear old and worn) old-fashioned high shaft cowboy boots. They have a narrow shaft bc the model thin rich people who can afford these boots don't want their legs to look fat. Folk want to show off what they just bought, so they wear them with the pants leg tucked in, (or in the case of ladies, with skirts) so you can see the boot designs. They are beautiful to look at but hideously uncomfortable, so no one wears them for long stretches- just out to dinner. Definitely not to dance in. (I went recently with some friends to a west Texas C&W dance hall that drew folk from a 5 county radius, and all the people there wore ropers to dance in.) Now I confess to owning a pair of these fashionable boots, too, (because I am a fashion maven) but I don't wear them in a heads-to-toe western outfit. That look spells "t-o-u-r-i-s-t" ! The Texas chic look is to mix in a little bit o' western wear with other items: some modern stuff. southwestern jewelry, lots of black, south American clothes or colors, and lately just a little bit of bling and /or animal print into the mix. The trick, as with any fashion ensemble, is to not overdo it: You are allowed only one "statement" piece at a time. That means only the cool boots, or the handbag, or one piece of big jewelry. Anything more is a fashion nightmare. By all means, avoid the white-trash version of this look: tacky over the top rhinestone encrusted, feather trimmed, zebra or cheetah print, cross embellished: jeans, rubber thong sandals, handbag, earrings, t-shirts, necklaces, watches, strollers, baby outfits, sneakers, headbands for your baby, Bible bags, cars, home decor......you get the idea. To put this on your dog, however, is retro hip amusing in a mocking sort of way and is totally acceptable.
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