Musar su Deuteronomio 22:5

“A man shall not wear a woman’s clothing” (Deuteronomy 22:5). [This is a negative commandment against] removing underarm and pubic hairs.

לא יהיה כלי גבר על אשה ולא ילבש גבר שמלת אשה . Rabbi Menachem HaBavli claims that this prohibition is designed to prevent opportunities for marital infidelity. The wearing of clothes of the opposite sex leads to sexual arousal and makes it more difficult to resist such temptation. I have found it written somewhere that if a midwife wraps a newborn baby boy in clothes once worn by a girl, that boy will grow up and become a womanizer. If the reverse occurs the girl is likely to become a prostitute. It is essential therefore to wrap a baby in a new garment, one that does not yet exude the residue of either a male or female who has worn it. This teaches that garments have a "personality" of their own. Garments worn by women transfer some femininity to a male who wears them and vice versa. In addition to this it is unseemly for a man who has been created by G–d as a member of the "stronger" sex to don garments of the "weaker" sex and thus indicate dissatisfaction with G–d's decision to put his soul in the body of a male.

Although the regulations about men not wearing women's clothing and vice versa evidently are meant to underscore that we are not to upset the divisions made by G–d when He created the world and decided who should be the משפיע and who should be the מקבל, there is yet another mystical meaning at the root of these regulations. The basic function of garments [prior to Adam's sin and the need to use garments as protective covers. Ed.] is to portray the glory of the wearer. This is why Adam, while in גן עדן, wore garments constructed of light, i.e. he radiated light, showing all those whom he approached that he was a creature of substance. Once these garments were exchanged for כתנות עור, tunics made of skin, their function became reversed. Clothing now was designed to hide the shame of the wearer. The idea of clothing was corrupted, as I explained elsewhere. We must also consider that there is a difference between souls which originate in the left side (diagram) of the emanations, i.e. the female side, and souls which originate in the right side (diagram) of the emanations, the male side. This profound secret is alluded to when we are told about the prophet Elijah fleeing from the renewed pursuit of Izzebel after he had slain the four hundred priests of the Baal and the people had cheered G–d. His flight is described in Kings I 19,3 in the words: וילך אל נפשו, and subsequently as: וישאל את נפשו למות. In the first example the prophet's "male" soul is referred to, in the second example the "female" source of Elijah's soul is meant. [The customary translation simply sees in the first words an attempt by Elijah to run for his life, whereas in the second version it sees a recognition by Elijah that his efforts have failed and that there is no point in his saving his life. Ed.] The Zohar in פרשת ויגש deals with the problem of how to join the male soul with the female, (cf. page 18 Sullam edition.)