I don't think he chose the hoodie because it was the ugliest, least stylish thing he could find (I think there's alot available on NFL.com that's significantly more ugly), but rather because a sweatshirt is pretty comfortable. If I was coaching, I'd be wearing the same thing.
I think you could use that phrase to describe most New Englanders. I know he wasn't born here but somehow he seems to have adopted our attitudes. I think that's why BB fits in here so well.