This shall not be done ordinarily or unnecessarily, for in some cases it may be lawful, as to make an escape for one's life. Now this is forbidden, partly for decency sake, that men might not confound, nor seem to confound, those sexes which God hath distinguished, that all appearance of evil might be avoided, such change of garments carrying a manifest umbrage or sign of softness and effeminacy in the man, of arrogance and impudency in the woman, of lightness and petulancy in both; and partly to cut off all suspicions and occasions of evil, which this practice opens a wide door unto.
Related Commentaries of Deuteronomy 22:5
Deuteronomy 22:5
5 The woman shall not wear that which pertaineth unto a man, neither shall a man put on a woman's garment: for all that do so are abomination unto the LORD thy God.