Age 7-1987...I was wearing traditional 80s stuff. That would be around the time I got my favorite t-shirt (probably 1988 or even '89, though) that said Nintendo on it and had the Mario characters around the logo. I have a vivid memory of riding my bike one nice fall evening as the sun set, thinking, "It's Friday night, I'm on my bike, I have my favorite t-shirt on, we're having pizza for dinner, and Full House is coming on. Life just doesn't get better!"
Age 14-1994...Don't remember oddly enough but I know pictures exist to remind me.
Age 21-2001...Very close to what I wear now at age 33...polo shirts, jeans, khaki shorts, etc. I always prefer short-sleeve shirts as I'm very hot natured.