Q 1: What is the ruling concerning a man who
wears women's clothing in secret?
It was authentically reported that the Prophet (peace be upon him) said,
"Allah has cursed women who imitate men and men who imitate women."
In another narration, he (peace be upon him) said,
"Allah has cursed effeminate men and mannish women."
(Part No. 24; Page No. 95) Men wearing women's clothing falls under this prohibition. Thus, this act is Haram (prohibited) even if it is done in secret, due to the generality of the prohibition.May Allah grant us success. May peace and blessings be upon our Prophet Muhammad, his family, and Companions.