Salam alaikum. Brother, what is the context of a hadith that says Prophet Muhammad (pbuh) curses men who wear women's clothes and women who wear men's clothes? Could it be taken literally or is there any condition that applies to the hadith to take effect? Thank you.
The relevant hadiths do not provide much context, so it is left to the scholars to interpret them:
The Messenger of Allah (ﷺ) cursed the man who dressed like a woman and the woman who dressed like a man.
Sunan Abi Dawud 4098 (Considered sahhi by al-Albani)
Allah's Messenger (ﷺ) cursed those men who are in the similitude (assume the manners) of women and those women who are in the similitude (assume the manners) of men.
Sahih al-Bukhari 5885
The common interpretation is that it is forbidden to intentionally act or dress in a way that is like the opposite sex. While some interpret this as meaning that, for example, women should not wear pants since pants are commonly worn by men, the proper interpretation I believe is that people should act or dress in a way that in their particular time and culture would make them look like the opposite sex. So it is not referring to any particular style of behavior or clothing, it is referring to anything that might confuse others as to one’s sex in their time and culture.