I'm so old I Remember when:

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Even Marge was a bra burner!
 
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".
:lau I heard it was as simple as that in prison they didn't give a damn about giving you pants that fit.
 

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