My entire wardrobe can be explained as the result of two influences: college and women.
College, because I went through a speed-affecting stage (not to be confused with the snorting-speed stage) during which I glommed onto whatever subculture seemed the most open to chain smoking and and free love. It turns out love isn't free and chain-smoking is the mainstay of all subcultures, so it doesn't matter which one you join; you pick the one with with the clothes you look best in. This turned out to be goth for me, but I didn't find that out until after trying neo-hippy, raver, punk, generic stoner, young republican (just the clothes), and various sub-subcultural derivations. The whole process took about six months, and left me with a variety of interesting clothes, with an emphasis on pastel black.
After this, my wardrobe was slowly whittled and occasionally expanded by the comments of beautiful women. This was an unconscious process until the summer of 2001. I was working as a lobster cook in my adopted hometown of Hancock, Maine, and due to a native population of about three hundred and a slightly larger tourist population who were all too young or too old or too uncreative to sleep with without creating a moral problem for someone, the only qualified girl I had regular, acceptable contact with was my coworker, the boss's daughter.
Prior to this summer, I disliked her. She had been ostensibly taking advantage of the crush a friend of mine had on her. In retrospect, she was just better at that particular game, so if she wasn't going to sleep with him and he still thought she might, she was within her rights to capitalize on the situation, and all of his friends, including me, were entitled to hate her for it. The system works.
However, lacking any other eligible females, I became a little obsessed with her. I'm still proud of how creepy I wasn't under these circumstances. To relieve the suspense, she wasn't interested, we never got it on, and we remained coworker-level friends. But before that got sorted out, she told me I was hot, but I shouldn't wear jeans.
I didn't wear jeans for five years on the strength of this advice, until a girl I was dating told me to wear more jeans. In between, I bought a bunch of blue shirts because a cute girl from Wisconsin told me blonds look good in blue, started wearing a trench coat because a bunch of bisexual punk girls told me it would be hot, stopped wearing the coat because a gay friend (in terms of utilitarian fashion, a gay man is almost better than a straight girl, especially in Manhattan) said it made me look anorexic, and bought some green shirts because another cute girl said I should wear green with my eyes.
When I shop, I take my girlfriend and let her pick things out. If I'm single, I take any available girl of the type I'm likely to date and let her pick.
Many of my friends say this is bullshit, and I'm whipped or have no fashion sense. They are absolutely right. If I'm getting sex from a single tap and I need to be attractive to tap it, she gets to choose what I wear. If I'm seeking new sources, the nearest representative of my desired source pool gets the baton. Because I don't care at all what I wear. I've been told to just wear what I feel comfortable in and let people come to me. This is stupid. Taken to its logical conclusion, everybody should just wear sweatpants and butt-packs. People who say this don't actually mean comfortable in a physical way, even if they think they do, they mean the sensation of looking in the mirror and thinking "I look good".
That sensation is utterly determined by public opinion. There is no other explanation that could possibly make sense. Good skin and emitting pleasing hormone are the sole elements of physical attraction that I can think of that might be universal. Optimal BMI and facial elements are changing constantly: merely in the accessible media of my time I've seen the ideal body weight go from Marilyn Munroe to Kate Moss, and now it's slowly creeping up again. The elements of the "perfect face" are perfectly idiosyncratic on both individual preference and which superstar model or actor or actress is in the spotlight at the moment. In the midst of these mood swings about what's physically attractive, fashion is a hundred times more insane. Fashion ranks only just below music in terms of how subjective it is divided by how ardently people believe it's not.
So everybody is doing some version of what I'm doing. They just do it on the level of pop media and social group. Women have the job done for them, as society at large is still male dominated, so the testosterone fueled flavor of the week is splattered over every available surface. Women know what men expect of them because men fall in line like lemmings to pursue popular visual stimuli. Women have more varied and particular tastes, because manhood is no longer defined, in acceptable discourse, as beating the competition into submission. Women have to rely on a more subtly embedded conscious representation of hormonal urges, so there's little to no telling what a particular woman will find attractive, unless you're a rich or famous man, because that's a clear indication you'll raise well fed children. Us non-rich, non-famous men have to be charming or look good according to local custom, so we consciously or unconsciously blend into our peer group fashion, making a special effort to mimic the peers with girlfriends.
I go straight to the source. Also, I have nothing personal or unique about myself that I could express through my clothes, except a jacket that was probably made on a drug bender and followed by the designer's suicide, and all that jacket says is "Yes, I paid money for this, and I probably was, and am still, on drugs." The part about me buying it because it must be the only one of its kind and it's a testament to how weird the human imagination can be goes unsaid. Because clothes don't speak. They just make you more or less pleasing to look at, and make it legal for you to go outside in populated areas. I have an impeccable sense for what looks good on women, and no sense at all for what looks good on me, because I don't have any real reaction to what men are wearing.
I can't even tell if my own face is good or bad looking, and I only look at that when I shave. How could I tell if my clothes are improving or handicapping my situation? My tactic comes less from logic than from necessity. But it works. And it's simple. And you never have to have a conversation about fashion again.