No, Yeshua never commented on anyone’s raiment.
As for the feather, there is little chance that we are getting sufficient detail in any news story to discern the full truth.
Yeshua’s very presence is a comment on all the law. He said, “Think not that I am come to destroy the law, or the prophets: I am not come to destroy, but to fulfil.” Do you think His silence on a matter means He is indifferent to the matter? Where does He speak out against homosexual behavior? Abortion? Taking drugs?
Do you think Christ walked about in woman’s garb?
Do you think Christ would have countenanced one of His disciples to walk around in woman’s garb?