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I guess the prison thing has some merit, but if my memory serves me correctly, people didn't always walk around with their pants down. If I recall, it appears to have all started after MC Hammer had a video come out where he was wearing real baggy jeans with the super-low inseam. After that, it appears that people started imitating his fasion, and since you couldn't just buy your normal pair of jeans with a really low crotch/inseam, than the only way to imitate that look is to wear larger sizes without a belt and sag the pants real low. Then over decade and a half (with prison influence) we ended up with fashion gone haywire.
Just my observation
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