It's normalized to the point where it's not likely to attract attention but still not common. I'd say it would be vastly more normalized than a man wearing a skirt for example.
Maybe he would, but he is quite an oddball in more ways than one. Both of his parents were Harvard/MIT professors, he is not silent about his political views (he at one point literally forbade anyone with a Trump hat to come in to his restaurant) so we shouldn't extrapolate from this one singular case one way or the other.
(excluding classical music)