The woman shall not wear that which pertains unto a man, neither shall a man put on a woman's garment: for all that do so are an abomination unto the LORD your God.
Read Chapter 22
Ambrose of Milan
AD 397
If you consider it truly, there is an incongruity that nature itself abhors. For why, man, do you not want to appear to be what you were born as? Why do you put on a strange guise? Why do you ape a woman? Or why do you, woman, ape a man? Nature arrays each sex with its own garments. Men and women have different customs, different complexions, gestures and gaits, different sorts of strength, different voices. ()..
God. Some take this literally, as the contrary practice is contrary to decency, and might be attended with very pernicious consequences. All know what noise was occasioned by the action of Clodius, who put on women's apparel, that he might be present with the Roman ladies at the feast of the good goddess. Yet others think that Moses here forbids some superstitious practice. St. Ambrose (ep. 69,) remarks, that in some of the mysteries of the idols, it was requisite for those present to change clothes in this manner, sacrum putatur. Lucian testifies, that men put on women's clothes at the feasts of Bacchus. They did the like in those of Venus, while the women took men's clothes in the festivals of Mars. (Jul. Hirmic. c. 4.) (Maimonides)
In the East, people honoured the moon, to which they attributed both sexes, and Venus in like manner. Josephus ( iv. 8,) believes that women are here prohibited to engage in warfare. Hebrew, "the vessels (armour) of man shall not be upon a woman. "Semira...
