*The author's Dan Post deerskin boots, broken in almost to the point of broken down.
[ed note - this is an original, great picture and a wonderful addition to the blog]
Regardless of what you may encounter at that awesome dive bar you occasionally visit with your frat bros because it makes you feel dangerous inside, cowboy boots are not back in style. They’ve been cool ever since the mid-1800s when today’s cowboy boot was born out of earlier, yet similar, cavalry and work boots.
I’m encouraged, and you should be to, that cowboy boots haven’t been considered especially fashionable since the 1970s. Disinterest and/or malice by the general public toward anything from ideas to footwear is a positive sign. If they become popular again, I’ll continue to wear them but behave worse than usual so as to create a correlation between assholes and cowboy boots.
In 2005, GQ’s Style Guy said, “to carry off cowboy boots you should be an actual cowboy, play one on television, or subscribe enthusiastically to that sexual specialty that causes certain taverns and pubs to enforce leather or western dress codes.” Style Guy’s witty ignorance could be attributed to the fact that the column was written four years ago, as people do gain wisdom with age. But more likely, he’s just ignorant and should be kicked with a cowboy boot, which brings me to my next and most important point.
Cowboy boots are the only choice for any situation where you need to look cool, but may have to kick the shit out of a member of your least favorite subculture (I suggest hipsters, neo-hippies, yuppie scum and anybody with a faux hawk – in no particular order).
But since this is a fashion blog, I will now move on to why you should do your kicking with cowboy boots as opposed to a work boot, or God forbid, a nice slip-on dress shoe.
Like Alexander’s answer to the Gordian Knot, the answer is simple but often overlooked: Cowboy boots are aesthetically pleasing in an absolutely un-ironic way, like the leg of a beautiful woman or the sound of a Chevy 350 through dual 3-inch straight pipes with no catalytic converters.
The cowboy boot is just as God intended, with no compromises for safety or concessions to focus groups. It makes no apologies for its stacked heel, mid-calf height and fancy patterns. For these reasons the cowboy boot should be respected as a fashion survivor, as relevant today as it was 100 years ago. Also, a decent cowboy boot is comfortable, kind of like a big slipper.
Beware, however, that the power of the boot should not all be exposed at once. Gentleman, I highly recommend wearing your jeans over the boots. Your jeans may crease gently on the toe of the boot, or may ride above the toe slightly; both are acceptable depending on the style of the jean.
Ladies, the artistic license granted due to your feminine nature means you may wear cowboy boots however you want.
A cowboy boot should be slim in profile with a thin leather sole. Materials and slight design variations are innumerable. I recommend brown leather or deerskin with a softer finish. You’re on your own from there.