Other than relatives giving me the doting, "oh don't you look nice!" at various church and school functions when I was young, the first time I remember someone commenting on what I was wearing was in junior high. It was a classmate of mine and he called me a "prep."
I can't remember exactly what I was wearing at the time (probably nothing more than a light-colored polo shirt of some sort), but I do remember that the comment was not meant as flattery. I spent my formative years in a small town in the midwest, where being good at sports and tough (yes, even in junior high) seemed to help your chances of success, at least on a social scale.
I went through high school without giving my wardrobe much thought, then went off to college in a different town and flew through different phases about as fast as I could. There were dabblings in goth (oh, dear), thrift store castaway (a mish-mash of skinny pants and horrendous print shirts, mostly entirely made of polyester) and finally the dreaded couldn't give a crap man-child phase (ratty pant 'n t-shirt, every day). That latter look stayed with me for a few years post college, as I landed with a dot-com boom-era job that allowed me to indulge sandals and 70s era t-shirts with faded iron-ons with worn army pants.
Where I've finally arrived has largely been caused by two things. First, and most importantly, I met a great gal who showed me that it's fun and yes, even comfortable to dress nice. Secondly, I got a job where I have to at the very least wear shirt with a collar every day.
The end result is a style that's not incredibly refined nor is easy to label. It's constantly morphing based on what I can find within my budget and an ever-expanding knowledge of what I think looks decent and works (although, sometimes the two still don't quite meet).
So, if I had to narrow things down, I'd say that my look is a combination of classic, contemporary, and cowboy, with a dash of kitsh thrown in for good measure. My tastes in regards to books, music, and art are largely similar, so it all makes sense, really.