There are some great stories and views here. I'll just tell some of my story and hope it adds to the mix.
My cultural background is in many ways quintessentially upper-middle class English (military family, private boarding school, Oxbridge etc.). Yet it's not quite as simple as that. My father's family are all from immigrant roots of one kind or another (a mix of Eastern European Jews, Irish, Americans, and probably a few others). My mother's family are all Highland Scots, with a dash of French huguenot and Welsh. And I've made this even more complicated by living in several other countries over the years including the USA and Japan, by marrying a Japanese woman and eventually moving to Canada.
What does this mean for my understanding of style? One, I grew up with miltary English upper-middle class norms of how to dress drilled into to me: highly polished cap-toes and brogues, tweed sports coats, particular shirt patterns and cuts in the English tradition, charcoal chalk-stripe suits etc. etc. Not necessarily 'stylish', but class-appropriate and 'acceptable' in their context. And no jeans. Definitely no jeans. When you grow up with this stuff, and you finally get out of the cultural environment, there seem to be two basic options: accept it or reject it. I rejected it completely. I became a long-haired hippy protestor. I wore dungarees, the cheapest stuff from thrift stores, no shoes. In other words, 'anti-style'. But during this time, as a result of the combination of an interest in history, in the 'waste not, want not' aspect of environmentalism and my thrifting activity, I became increasingly fascinated by the history of clothing, by vintage, by dandyism, by mods, and fashion as self-expression, rebellion etc. So I changed. At first I was entirely indiscriminate and threw anything together that seemed to have some 'quality' that I liked. I knew nothing, but I'm someone that doesn't really have much of a sense of embarassment so my general process has always been 'try it and see'. Now, I'm a fair bit older, I still have that experimental urge but I've tried to think about what was the best of what I grew up with, in other words, my cultural 'basics' of style - that is a bigger point BTW, despite the emergence of a Euro-American set of clothing norms, I still think there are different cultural understandings of style basics. Howewer, I'm also reconsidering how to think about my deeper cultural roots, and how and whether it's possible to reflect all or any of these in clothes. And, I've been quite seriously affected by the commitment and attention to detail, that the Japanese show in street fashion, not that I am ever going to be street fashionable - it's the attitude I like. Last point, I don't have the kind of disposable income some here do to spend on 'essential' sartorial items, let alone more frivolous things. I still have to rely on sales, second or third tier brands, gifts, second-hand, thrifting and vintage. But then perhaps what someone else here called 'mix-and-match' really is my authentic culture...
Finally, when you're in the cultural position I'm in, you can't take yourself too seriously. So, if style is about that perfect balance of attention to rules and details and personal self-expression, in other words about communication, I am interested in how one can establish gently humorous cultural reference points in clothing, things that might make people smile without either being either so obscure or so blatant that they just come across as failed camp, ugly mistakes or again, anti-style. God knows, the worst kind of humour is the kind that only amuses yourself and as far as my (never again) attempts here have gone, well, I can't even spell 'humor' properly, can I? (Anyway, on that particular subject, I started a thread in SW&D to ask, with apologies to Frank Zappa, whether humour belongs in fashion...).
Edited by FlyingMonkey - 9/30/11 at 7:04am