When you don’t have a lot of money, you often get hand me down clothes that don’t fit. You then make do with what you have. And if a group in that situation adopts it as part of the culture, it can become cool and starts to be taken in fun directions.

Look at ripped jeans. It used to be a sign of poverty (you can’t get new jeans and your parents can’t fix them?), now they sell it as a feature.

That said, it’s no more ridiculous than ties and buttoned collared shirts. Asphyxiation is a weird cultural fashion.