I'm not sure if its a nessecarily a generational gap thing, although I'm sure that plays a role. I was born in 1979 and grew up during the 80's and 90's in a very rural area, most people were either farmers, loggers or factory workers and with such a large blue collar population "fashion" was never important. Growing up I remember most men (aside from winter coats and such) always walked around in their work clothes, jeans, tshirt/button work/flannel shirt, baseball hat and work boots in fact most would be out and about while on a break or at the end of the day stinking to high heaven and caked in dirt...or something worse. Unkempt beards and mustaces were common and nobody gave a shit what their hair looked like, it was kept short and usually under a hat anyway.
The only time anybody really ever "dressed up" was on Sunday at church and then it was the nice jeans, the clean shirt and the not so beaten up work boots....or my favorite the old farmers special flannel shirt, dicky work pants (often green), boots, green tie and sports coat. Anybody dressing any nicer then that would have stood out like a sore thumb.
I would say the "style" was handed down to our generation and judging from how my grandparents dressed and seeing old pictures I would imagine older generations did the same. Its certainly influenced how I dress and look, I always feel out of sorts in anything other then jeans/shorts & tshirt and you wont find me in much else unless I NEED suit/tuxedo or something for work or special occasions.
It would seem to me that how people dress is based as much on where you live, how much you make, what you do for a living...class structure and all that as much as it is generational. Although I do agree that with each passing generation it has become more acceptable to dress down and neglect your personal appearance.
EDIT: How in the hell did I manage to write that much about rural fashion?
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