Most of junior and senior high school for me was spent at a private school, where I had to wear khaki slacks and a white shirt every day. The upside was that I didn’t have to think too much about what to wear every day; the downside was that when my friends and I were out fartin’ around, since there weren’t very many private schools in Houston at the time, if something happened, we were pretty easily identifiable as St. John’s students.
I was a teenager and young adult during hippie times, and tended to wear the uniform (bell-bottom jeans, hiking boots, t-shirt and army jacket), but I also played in several bands, so I had some flashy stuff (platform boots, muslin blouses, sparkly jacket, etc.), but I never wore that stuff to a day job.
When I finally went off to college, the wardrobe mutated from some hippy/flashy to mainly cheap jeans and t-shirts, with the exception of a number of grey dress shirts that the Austin cab code required that I, as a hack, wore.
When the corporado existence began, I started off cheaply with the khakis and white shirts reminiscent of high school, along with a blazer and (a very few, to begin with) neckties. I soon added grey, navy and black dress slacks, along with some pastel button down cotton oxfords. As soon as I could afford it, I began acquiring suits, and I spent the next decade and a half wearing (gradually becoming flashier) suits to work. My leisure attire tended towards jeans and the same dress shirts I wore with the suits, although the occasional t or polo worked its way in, along with, oddly, several sleeveless black t-shirts.
Finally, almost a decade ago, I began to relax on the suits. Now I wear dress slacks or khakis, with button down cotton oxford dress shirts, to work. Weekends are spent mostly in shorts or jeans, with a t-shirt or a polo.