@freemo well they don't hang there pants THAT low, it wouldn't be aloud. But hung down a bit.
That's where it all started.
Why straight guys think it's gangster, I have no clue. I think 99% of them have no idea what it really means just like most people don't know swag stands for "secretly we are gay" and started in the 80's as code in the gay community.
@Wetrix I dont buy it for a second, especially considering that the prison-origin story has mutate several times since its original telling. Used to be explained because belts werent allowed in prison, now its explained as an explicit initiation rite. Neither seem plasuable to me and there is no good source linking it to prison.
Earliest evidence of it was from the skating and hip-hop communities in the 90's. Its connection with hip-hop may havee made people assume or make up a story about prison as a result. It seems more likely it was just artists dressing absurdly on stage, as they tend to do, and people emulating it.