My style evolution, basically, is a lot like the stories of many people who come to this site, but I started way earlier. I think I got into clothes around 1995, so this was before the 'internetz for cluthinz' that is so convenient today. I was probably attracted to fabrics, and i didn't know the first thing about fit. Then I got to college and started traveling more as well, and noticed how much better non-Americans dressed. I visited Japan for the first time in garbage American clothes (and this was at a time when Japanese streetwear was really strong) and they just swagged all over me, so that was about the time I knew I definitely had something to aspire to, but I still struggled with it back then, around 2000-2004'ish, before more widespread discussion on the internet about clothing started, and due to the fact that they just don't really sell my size clothing in America, especially not back then. Small timeline: 2002: I'm wearing a Burberry mac that was technically two sizes too large for me, but realistically cut for someone 50 lbs heavier and from circa 2000, a RLPL shirt from the mid-90's I couldn't let go of, J. Crew trousers, brown Bruno Maglis with a Norwegian toe (which were actually pretty nice)
2003: Paul Smith graphic tee, oatmeal henley I think?, J. Crew pre-distressed jeans, Clarks, Hermes manbag - this fit sucks, but I think the jeans fit is kind of interesting now
2004-2006: I learn about Japanese denim from a magazine, can't find any of it at the time, search on the internets and I come across sufu and styleforum, lurk for awhile, change almost all the brands of clothes I buy and foremost I get a sense of fit to suit my body type. mid-2007: this is where I start amassing clothes that suit my body shape, because I have been the same size all along, I'd just been wearing everything two sizes too big until about 2005 - yet as you can see, I'm still lost about what to do with my hair. I'm at corny Asian styleforummer/sufu'er stage at this point.
2007, 2008, growing hair out, the swag juice starts to flow, the black leather jackets start taking over and the uniform starts to blossom:
(experiment with cockbib for a short time)
etc, etc, the hair got long, everything locked together, swag juice got thick. Kept a pretty constant style for the past couple years now.