HA! I love this thread.
I wore these in the early 80's and then again in the late 90's, They came back.
I believe Jr High was when it was cool to tight roll your jeans
It was cool to wear your Eastland shoes with your tight rolled jeans.
I also had a period where I got a "Rachel" Hair Cut, but never styled it right:
I was totally Angela from My So Called Life, She (and I) dressed like this at first:
Then started dressing like this:
I even had that exact same plaid, flannel dress. I wanted to dye my hair the same color, but my mom wouldn't let me.