last time he was on FOX he talked about how he was a millionaire, brought it up several times. he's hardly trying to hide it from anyone from what i could see.
he's always impressed me as someone who had money--even when he was filming the docos on Flint. IIRC, both the second film and the television show frankly speak about how he lived elsewhere, now had money, more than the average guy, etc. i've never seen his clothes as condescending affectations. rather, i suspect that, like most people who've been tormented by those who sneer, it's about all the guy knows how to wear given his weight and height. some people just don't feel comfortable in other kinds of clothes and some men will never like wearing big men's clothes that are supposed to "hide" the gut but are just too obvious. so, they don't bother and stick with big guy's jean and a jacket --that's supposed to hide the gut and the fact that he doesn't have a butt to keep his pants up so his shirt comes untucked.
makes sense to me.