Seriously, this needs to go into the Tweed Thread. Insane.
I think he's not pulling them off well because a) those pants don't look like they were made to be worn that high and b) it looks like he hiked them up so high they ended up being short.
Other than that, I think that's where the waistband on dress pants should always fall, specially when wearing a jacket with a low button stance like that one.
Well, seriously, I don't think he's actually wearing them that high. I think the low button stance is contributing to the Urkel effect, but the pants seem to be at his waist, not above his ribcage.
And I believe thin people actually look better than phat dudes in a high rise. A bigger guy with pants hiked up high will look even wider because of the horizontal to vertical dimension ratio of his apparent upper body.. a thin man will look more proportioned. Unless he's got really long legs.