On dress, I honestly don't care. He's not supposed to be in the public eye, he is a back room "boy". He can wear what he wants. It is much more important as to what he does, than what he wears..... and there we have an issue.
Lots of non-customer facing roles now have casual dress. In many companies even at high level, most executives now wear smart casual, shirts and chino's. Very rare to now wear a suit every day.