Levi 501's 4 Life.
I've worn them almost my entire life, first pair I guess was somewhere around 13-14.
Hoodies the same except they were called 'kangaroo shirts' when I was a kid.
And Adidas Stan Smith sneakers and Chucks - I was wearing Chucks long before they became trendy.
My dad was a suit and tie guy, had to for his job, his casual clothing was embarassing - he would wear old suit pants and an old dress shit and old dress shoes, or worse, my mother would buy him colored golf type polyester slacks - looked so bad. So me and my sisters bugged him for years and years to try wearing jeans, he refused saying they weren't even comfortable, the fabric was too heavy and stiff. He finally relented and tried them when he was about 60, we bought him some faded 501's - and by the end of his life that's all he ever wore.
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