No, way. I can't stand that look. The guys that sag their pants also waddle like penguins. They look ridiculous. Trust me no body admires that style, a great portion of the people think it looks disgusting.
Sagging pants has been known to be a sign of homosexuality in prison and it means your booty is open for... you know what lol. Um other than that it's extremely unattractive so I'd recommend that you don't, just my opinion.
I remember I saw a prison documentary showing the older prison mates talking about the new generation of prison mates and they were saying how the new guys are just asking to get screwed in the ass and if they ever need to run away from danger they're fucked...
... If you wanna say you're up for a gay interaction, go ahead. Doing that in prison means you're available. ... Plus it's dumb and a lot of people really don't want to see what color your boxers are. Doesn't matter if they're the coolest pair of underwear in the world.