When I was in my early teens, I used to wear skirts over jeans all of the time. like Juno in Juno, only not even remotely cool.
I also used to wear really baggy jeans, and these ugly cheap t-shirts that were usually black with weird designs, like skulls or rainbow swirls or emoticon faces. My favourite one was black with a white frowny face and the words “cheer up emo kid”.
At the time my hair was cut in a short bob with a fierce fringe. I had cherry red streaks, and would wear my hair in pigtails all the time. I used to wear choker necklaces and as many bracelets as I could fit on my wrists.
For warmth, I wore hoodies constantly, and my favourite was a big black and grey knit sweater with a hood. My other jacket that I would wear until it was literally falling to pieces and the buttons all dropped off, was a second hand grey corduroy jacket.
This was my look until I was about sixteen years old, and even then the baggy jeans stuck around until midway through last year when I finally gave in and made the switch to skinnies.
Skirts over jeans was something I used to think was so cool. I have no idea why.