Please explain this weird teenage fashion

Yup. Brought on by Kris Kross

When I were a lad in the seventies, and at school in rural Scotland, our reaction to the punk stuff appearing on TV and in the charts was to roll up one leg of the school trousers, untuck the shirt and tie the school tie round the head. Obviously, this was only at playtime - the teachers didn’t really approve of this in the classroom. Anarchy in the UK!

Bolding mine Apparently neither are the kids. I still see it everywhere. I recall seeing it right after I graduated from high school in '90. Why won’t it die?

Right. But the primary advantage to wearing one’s pants backwards (stealing this bit from a comic on VH1) is that you don’t have to pull down your pants when you need go Number 2.

I did this a lot as a teenager and still sometimes do it at 24, though with a jacket instead of a sweatshirt. It had nothing to do with fashion or even laziness, I just had cold arms and didn’t want to fully put on the jacket, lest I get too hot (I have a thing about temperature regulation). I figured anyone observing me would guess as much. It’d have never occured to me that it would provoke someone enough to post about it.