From the perspective of Jewish law, it is a big sin for a man to dress like a woman.
This whole transgender movement is repellent for the traditional Jew. Orthodox Jews can’t stand this stuff. It turns the stomach.
Orthodox Judaism is structured around separations between men and women, Jews and Gentiles, adults and children, holy time and secular time, etc. The Hebrew word for holiness is “kadosh” which literally means separate.
It is discombobulating for me as a convert to Orthodox Judaism to see how non-Orthodox Jews in Hollywood, the media and academia are pushing the transgender agenda. It’s as weird as finding that the pornography industry is controlled by Jews as pornography is the very opposite of the holiness and familial solidarity that Orthodox Judaism seeks.
Are things Jewish because some Jews do them or because Jewish texts endorse them? There are no traditional Jewish texts that support the gay and transgender agenda.