Some time ago, I started reading grown-up man magazines like GQ and Esquire. I don't buy a subscription, I scavenge them from book store shelves and from libraries that are edgy enough to carry edgy grown-up man magazines.
At the heart of it, the man-magazine is just like a women's magazine. They really are just men's fashion magazines. They're man-Vogue. They're man-Cosmo. The similarities abound: They sell themselves by putting skinny chicks on the cover; They offer tips on fashion; They fill pages with dumb quizzes. The man's mag just gets away with content that is considerably just as inconsequential as that of a women's magazine, but somehow well-suited to the man.
Mixed in with all the man-tailored Cosmo-content there's actually some good writing. That's why I pick them up: I read the articles. And while I'm at it, I try to take a look at what is and is not cool in men's fashion. I am one of the last people on the earth to go to for advice on what to wear. I feel stupid just using the word "fashion."
When I was in Junior high, I showed up to school one day with my oversized stretched-neck Taz t-shirt tucked into my jorts (jeans + shorts = jorts.) I went up to a table of friends and Greg Borst called me out on my miscue: "Dude. Untuck your shirt, that is not cool." So I untucked my shirt and told him I was well aware that it wasn't cool. Then I probably changed the subject. But that day, I took a tiny step forward in dressing well.
Sadly, that was the last step forward I ever took. I have been style-ly stagnant ever since. My style from then until college graduation was the t-shirt with the jeans. And that's a big part of who I am: I don't like to stand out. I just want to blend in.
Unfortunately, when you start to interview for jobs and eventually join the working-class, you can't blend in. You have to woo employers by looking like you care how you look (I actually have to shave more than once a week now, and might occasionally wear a tie) and dressing in appropriate correspondence to the ever-vague "business casual" (or, as those of us not in-the-know say, "biz-cazsh".) Hence, my increasing interest in not looking like a buffoon.
I've turned to the man-mag for help because I recently concluded that I have the following things going against me: lack of practice in looking "nice" for two-plus decades (save for pre-church motherly spit-bath and approval), color-blindness, and general apathy. I'm content with jeans and free t-shirts from Team Building Exercise 1999, and employers want dudes who aren't content with jeans and free t-shirts from Team Building Exercise 1999.
Except, I've found it really hard to accept what the man-mag promotes as fashionable. They usually get a couple of male models, probably skinny chain-smokers, who would probably look okay in an over-sized, stretched-neck Taz t-shirt and jorts. (In fact, I might have seen that in Esquire once.) They get a bunch of free clothes from designers who sell t-shirts for $80 and jeans for $350, and match it with some other designer's $250 sweater (which, altogether probably cost more than I've spent on clothes since my big shirt-untuck in Junior high.) and stick them on the skinny chain-smokers. Also, they get a bunch of stuff that normal people just do not wear - poofy shirts, aviator jackets, other stuff I've never seen before and can't categorize. They take pictures of them looking like Zoolander frolicking in some park somewhere.
My thoughts: Fashion is moot if you're a model. If you're professionally good-looking, then you probably aren't the one to convince me that this shirt will make me look good. You want to sell me a sweater? Put it on an ugly dude (some portly, unshaven, and dissheveled oaf - not unlike myself - would work) and show me that it makes him presentable. Then, maybe I'll buy it.
But not for $250.