Deuteronomy 22:5

Why did God call it an abomination for men to dress like women and vice versa?

PROBLEM: What is wrong with wearing the clothes of the opposite sex? Isn’t this just a matter of cultural preference, with nothing intrinsically immoral about it?

SOLUTION: God’s design here was apparently to make it possible to distinguish one sex from the other. Without distinctive clothes and length of hair (see comments on 1 Corinthians 11:14), the sexes could be more easily confused and the bounds of social and moral impropriety would have been more easily transgressed. Of course, which clothes are masculine and which are feminine will be determined in large part by the culture. But whatever the case, transvestites were hereby excluded.