I am at a major disadvantage in terms of clothes shopping in that not only am I for wont of a girlfriend to help dress me, my own tastes generally gravitate around “professor character from Broadway musical.” Which of course only helps to postpone finding a girlfriend to stop me from buying so much argyle. Its a vicious cycle, like poverty, or or remembering to buy books on mnemonics, or cocaine.

To compound matters my body is more or less the shape of a meerkat, and so even if I were capable of remembering basic details like my waist length or noose measurements it would still be difficult to dress myself in such a way that I did not resemble a scarecrow practicing law.

I do have excellent sartorial tastes and know oodles about blazers and cufflinks, but when it comes to casual wear my wardrobe has for several years basically been a random assortment of trousers and collared shirts from relatives who lost sufficient weight before dying. In the last six months it’s entirely possible that more people have seen me naked than wearing a t-shirt.

I amended my casual wardrobe from “deceased hand-me-down” status to “normal” for the first time in 2008. After leading a walking tour in Edinburgh half a dozen sixty-year-old Scotsman puttered by, all dressed more or less identical to me. The similarity was so uncanny, so chilling, that I resolved to finally admit my friends’ fashion opinions were valid and buy blue jeans for non-agricultural purposes.

This is why denim exists. You morons.

I say “non-agricultural purposes” because, by the way, that’s why denim exists. My first job out of college was as a ranch hand, where denim was both common and practical. In my home state it generally makes sense to have denim on hand because you’re going to be weeding, fishing or shooting a geriatric horse at some point during the week anyway and it helps to own durable pants. Why and when urbanites decided to recreate farm breeches into upscale designer apparel remains a mystery to me. (My best guess is that some moronic yield-based deficiency payment provision of an Omnibus Farm Bill lead to a denim glut in the 1970’s, compelling Madison Avenue to capitalize on mountains of otherwise unneeded work duds.)

So in Edinburgh, aware of my need for a wardrobe upgrade, I visited a store called H & M which caters primarily to vampires and women who appear very bored and text a lot. I managed to find a pair of jeans which fit poorly enough to constitute as fashionable, purchased them on the spot, and wore them regularly ever since. In fact I discovered that if I combined my usual collared shirts and blazer with the new trendy blue jeans, people mistook me for being in my mid-thirties instead of my early forties (a clear upgrade, as I am in my twenties).

See? See how cool these blue jeans looked whilst walking?

Recently the jeans died. The cloth ruptured over the left knee, and a hole in the fly began to grow at a pace indicating a far more interesting and spontaneous sex life than those trousers ever saw. For the second time in a decade I was forced to purchase new blue jeans.

I asked my friends if there is a Jeans Store, and they said that the best bet is the mall. So this is my first piece of advice to equally clueless men: blue jeans live at malls.

Now, guess how many sorts of blue jeans there are? Beforehand I thought there were probably three: skinny, normal, and black.

It turns out that there are roughly three hundred and seven.

That number sounds daunting but a lot of blue jeans are clearly designed for someone else. For instance, the first store I visited sold blue jeans exclusively involving glittering sequins and stitching which I think glows in the dark.

The next place, Lucky Jeans, sounded like a much safer bet. I stepped in and stared blankly at a wall of dyed cotton until a salesman finally approached me.

“My pants broke,” I explained. “I need pants like these,” I said, pointing down at my blue jeans with the holes at the knees and crotch, in order to note which pants I was referring to. “I would like not-broke jeans like these, with no holes, please.”

The helpful attendant quickly located jeans which did, to their credit, look much like my own defunct pair. They were “boot cut,” which means they flare out at the bottom slightly. (I had been calling these “bell bottum” for the last four years but “boot cut” is apparently the technical term.)

A woman they pay to stand in the dressing room and tell people how good their asses look smiled dazzilingly once I tried them on and assured me that my ass looked brilliant in the fresh trousers. My ass, she assured me, would cause traffic accidents and easily outpace Mitt Romney in the polls. Full knowing, of course, that I do not actually have an ass. I have negative body fat. If I indeed have glutes which could handsomely fill out denim contours in a muscular bubble, then they are obscured within some kind of quantum universe only the smartest PhD fashionistas can discern.

My sales guy located me and, likewise, agreed that I looked amazing and that my ass was magnificent and the boot cut I had chosen was so stylish and smartly-crafted that it would probably inspire someone to cure leukemia.

“Looks good. How does it feel?”

I walked around in the jeans for a little bit and noted that, overall, they felt incredibly tight. Particularly in the crotch. I didn’t mind tight shins so much, but I could see “painfully tight crotch” becoming an issue. I would never be able to sit down, for instance, or one day sire children.

“They’re a bit tight in the crotch,” I admitted. “Once they’re broken in, do they ease up and get comfortable?”

The salesman explained that no, these were cool jeans, and cool jeans by definition make your penis hurt. You just sort of acclimate to your testes living in a vice grip of textile, comforted psychologically by the fact that you look so unbelievably cool that cocktail parties form around you spontaneously like thunderstorms.

I considered all this and walked around a little and checked in the mirror to see if I really did look Hollywood-level cool. I finally decided that I would only buy such a pair of jeans if they were so magically, mind-alteringly sexy that random women in bars and escalators would frantically tear them off me before the crotch pain could become an issue.

So next I went to Nordstrom’s. A salesman located me at the pants section and I explained my predicament, that I needed (apparently) “boot cut” blue jeans which also did not hurt my crotch when I did certain activities such as breathing. He diligently selected several hand-crafted pairs, all of which he explained were of far better quality than the Lucky Jeans I had foolishly tried on earlier. These new jeans were made of sturdier denim and so would last longer, they were crafted in better sweat shops by smarter children in third world countries more fun to visit than the shitty third-world countries Lucky’s was slumming from, they could re-enter the earth’s orbit without damage, repel bullets, were triple-distilled, etc. And, to his immense credit, they did not hurt at all.

“I’ll take them!” I said. So I slid my debit card across the counter to this ominously happy man and purchased my new $247 blue jeans.

I’m aware that $247 sounds like a lot. But at the time, I reasoned that, as I only buy the things once per pope, they’re kind of a long-term investment. Like a car. Just to be safe, though, I called my mom, who explained to me that my overall goal should be to find blue jeans which cost less than $60 and did not hurt and had a length less comical than the last time I bought pants on my own with a three inch gap from cuff to shoes.

So I returned the millionaire jeans and headed to Macy’s, where yet another salesman snagged me. He found the boot cut jeans which I’m told are hip and trendy, and I tried them on but noted that they felt funny because the waistline was actually below my waist.

“Oh, they’re all like that,” he explained. Because apparently, despite the anatomical structure of human beings, we now design our pants to fit below the hips, that way they cannot conceivably be worn in a natural manner. They will either fall down comedically and land you in prison, or must be tight enough that the skin will puff out over the edges and convince any young woman who dares experiment with such a reckless style of pantswear that she’s pudgy.

Conversely, you can buy these others jeans, called 501’s, which are like regular human blue jeans where the belt goes above your hips and you can walk around in them and they don’t fall down or cut off circulation to your legs or anything.

Since both types were on sale I bought both, which should last me through the next two and a half popes. When these pairs finally go kaput, I’ll probably have a girlfriend or a butler who can advise me in such matters. If not, I’ll just cut off my legs with a chainsaw and figure out how to match prosthetic limbs with belts.

How To Buy Blue Jeans If You Don't Have A Girlfriend