I'm so old I Remember when:

Very true. And boys/men wearing pants down below bottoms.
As it was related to me, that trend started in the lock-ups so the buttocks wouldn't get chafed as the pants were (less than nicely) pulled down. Later, the tend was to advertise the wearer was available to other inmates. By the time the fashion made it to the streets and spread to the general population, it was aptly named "prison chic".
 
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