That sag is so hot, in that second vid it's almost as if he wants us to see how low he's sagging, by subtly lifting his shirt a bit in some parts.
And when his trousers get too low, he just adjusts them a tiny bit but makes sure that they're still at the 3/4th ass mark which is very low. I'm talking about 2:38 in the second vid. I can't get over how hot that is, I love when guys do that lol.
Unfortunately I think he stopped sagging after 2013/14. In 2014 he still sagged a bit but wore them much higher, now I think he's stopped altogether, but I might be wrong.