LOL Kim, I'm guessing I'm a bit younger than you, but I have many memories of being in middle school and wearing black leggings with adult XL t-shirts in crazy bright colors (or remember hypercolor?

). My sister was in high school at the time and was one of the ones wearing ripped jeans, converse or doc martens, a band T-shirt, and an unbottoned plaid flannel shirt on top.
When I was in high school I wore those enormous wide-leg jeans and platform sneakers, and lots of hoodies. I actually miss my platform sneakers. Now I realize how short I am! Although I don't think I'd ever wear those huge-leg jeans again. It looked like they were trying to eat me!

I thought the wide bottom would balance out my wide hips and big butt. Nowadays I stick to boot cut.
Actually I used to wear a lot of tees with cute pictures or sayings on them (I have one with a picture of a smiling loaf of bread that says "Loafin' Around" on it). I tend to not wear those much anymore, since they are inappropriate for work even though I have a casual workplace, and I have so much other cute stuff to wear on the weekend.