Let me get this out of the way upfront. I’m bald. Chrome-domed. When I wear my standard black hipster turtlenecks on Fridays, I look like a roll of deodorant.
In other words, I couldn’t sport the current hairstyle craze, the Nazi-Youth/Kim-Jong-Un do even if I wanted to. With nothing but a few lonely wisps to contrast my buzzed or naked sidewalls, I’d look more like Howie Mandell than the Dear Leader.
Come to think of it, though, I could cop a toupee and maybe pull it off. The trouble with toupees in general is that it’s hard to match the fake hair in color and texture with the wearer’s authentic hair. Indeed, the Nazi-Youth/Kim coif might make a toupee look more realistic, so never mind. If I really wanted to, I could affect the look.
But the thing is I don’t want to.
Because IMHO it looks like shit.
According to the dilettante scholar’s best friend, Wikipedia, the undercut originally signaled poverty, the not-so-handiwork of makeshift barbering. Indeed, when I see some guy or gal sporting the undercut, I imagine a barber with clippers abuzz succumbing to a massive heart attack or being stricken with a grand mal seizure as he falls forward desecrating the side of his customer’s head.
The anthropological question arises: Why do prosperous people want to affect the look of poverty, spending their hard earned (or in many cases inherited) money of hack-job haircuts and ripped jeans?
The short answer is “I dunno.” However, Jackson Lears in No Place of Grace: Antimodernism and the Transformation of American Culture, 1880-1920 writes about a “disaffected cultural elite” who try to appear not so boringly bourgeois by mimicking hipper cultural milieus like Seattle’s ‘90’s grunge scene. These elites co-opt the workingman flannel and ripped jeans look of Kurt Cobain and Eddie Vedder, but the overlords of capitalism eventually cash in, mass producing and selling prepackaged rags to moms and dads who want to provide their children with the latest, most popular commodities. These are the same parents who write $30,000 tuition checks to top tier independent schools so their sons and daughters can get into elite liberal arts colleges. The idea of Bennington (the boy) and Madison (the girl) one day wearing their jeans out via manual labor is a horror the equivalent of shopping at Food Lion. Meanwhile, since we live in a youth culture, these moms and dads are dressing like their teenaged children. This popularization of the style, of course, renders it uber-unhip so the hipsters are forced to take things a step further and cover every square centimeter of their epidermis with tattoos or to take a weedeater to their locks, and guess what, the next thing you know your CPA looks like he got his hair caught in a Veg-O-Matic.
This pattern, unfortunately, doesn’t spill over into the automobile industry. These people don’t tend to buy used Saturn sedans or vintage Yugo GVs to look hip.
To quote the great Kurt Cobain, “Whatever.”
One Last question. At what thigh-circumference do “skinny jeans” become “tight britches?”
 Otherwise known as “the undercut.”
 A fascinating study I highly recommend.