but this place is just right.
I recently bought a pair of cowboy boots. I did not need them, but I definitely really, really wanted them. I always dreamed of being a cowboy when I was a kid, and as an adult, I enjoy wearing clothes that are a hair shy of “full costume” on the ridiculousness scale. And given that cowboy boots were “in” a whole three years ago, I figured it was high time to hop on the trend. Or something. The point is that one day, my brain told me to buy a pair of cowboy boots, and I managed to do so without agonizing too much over it. Here are the boots. Yee-haw.
I ordered these off the internet, just like they did in the old West (back then, everybody referred to “the internet” as “the Pony Express”). They are technically called “roper boots,” which are like cowboy boots but a little shorter and less “I’m wearing cowboy boots”-y. I can wear them with pants that are not specifically boot cut jeans, which is good. But when they first arrived at my door and I rushed to put them on, I made a horrifying discovery: You know how in the Toy Story movies, if you pulled the string on Woody’s back, it’d make him say, “There’s a snake in my boot!”? Well, these boots felt like they were stuffed with snakes, and the snakes were constricting the flow of blood to my toes.
I was faced with a dilemma. The site I’d ordered from told me to get the same size that I wore in dress shoes, which I did, yet they were too tight. Was this normal, or did I need new boots?
Because I am deeply lazy and cannot trust myself to return something I purchased online, I decided to hop on my horse and ride it all the way to Reddit, where I figured there must be a thread where other boot owners had offered some tricks for stretching too-tight boots out. After all, Reddit is a website where no matter what question you might have, the odds are there is someone who has already asked it, and that there is a resulting thread where at least one person has given a helpful answer. I was hoping that some weirdo on one of the site’s menswear subreddits had bought cowboy boots and already dealt with this issue, but instead, I found something much, much better than that: an entire subreddit dedicated to cowboy boots.
As you might be able to guess, the denizens of r/cowboyboots like to show their boots off. Some people are just excited about their first pair, while others have alarmingly large collections. Cowboy boots can come in a variety of materials, ranging from conventional leather and suede to “exotics” such as lizard hide, sharkskin(!?), and, as pictured in the above post, snake, ostrich, and crocodile leather. The weirder the material, the more ornate — or at least more expensive — the boots tend to be, with a pair of handmade alligator-skin boots from Lucchese, the gold standard in American cowboy boots, costing around $13,000.
Though my boots are very much on the cheaper side of things, I get it. Cowboy boots are nice. Even when they’re too tight, it’s almost comforting, like a bear-hug from an overeager aunt. Many boots were developed for a specific purpose or job, but few of them are still so closely associated with their origins the way cowboy boots are. They can cost a good bit of money, but for some people, they’re an investment, something you buy once and keep forever, to be resoled and reconditioned maybe, but rarely replaced. The most touching posts on r/cowboyboots tend to be from folks who’ve been  wearing the same pair of boots for as long as I’ve been alive.
As for the issue with my own boots, it turns out that cowboy boot tightness is a matter of taste: some people like them to feel comfortable right out of the box, while others prefer to order their boots a little tight and let nature take its course. According to this very helpful thread that I consulted, a pair of calf-skin boots like mine will stretch to fit the shape of your foot. Thanks to this other thread, I decided to start out wearing my boots around the house with thin socks, and once that felt comfortable, I switched to thicker socks to stretch them out even further. This break-in process can take time, and even be painful, but as Patrick Swayze, playing the notable cowboy-boot-wearer-slash-bouncer Dalton in Road House once said, “Pain don’t hurt.” A little bit of effort now is worth it for a lifetime of boot further on down the trail.
Most of the people who post on the subreddit, it seems, live in places like Texas and Oklahoma, where it’s considered normal to wear cowboy boots every day, even if you work at an office or a hospital instead of on a farm or ranch. But there are cowboy boot guys and gals all over the place — the midwest, Canada, Europe, probably the moon. It takes dedication and a little sacrifice to become one, a willingness to endure physical discomfort and potential mockery from your peers assuming you are not in cowboy boot territory. As I continue to break my boots in, and long after, I will keep popping into r/cowboyboots, a place where people cultivate relationships with their boots strong enough to encourage me to work on my own. With enough practice, one day I might be a real cowboy, just like they are.