613 Mitzvot
Negative Mitzvah 39 & 40
Women not to wear men's clothing.
Men not to wear women's clothing

YHVH created everything to be unique, for it is written that He created everything after their kind (min in Hebrew, meaning portion). (See Bereshit/Genesis 1:25). Men and women are the most important of all the creations of YHVH, and He made them with unique qualities. YHVH wants us to maintain our uniqueness in the way we dress.

In bibical times, the clothing that men and women were basically similar. Both men and women wore an under garment or tunic, which was bound by a girdle. They also wore an over garment, a mantle. The Torah uses the phrase (k'li-gever). The word (gever) is translated male and it refers to the strength of a man. It can also be translated warrior, refering the ability to figh, since the root means to prevail. The word (k'li) means instruments or accessories. It is often used to refer to instruments of war (Talmud Bavli Nazir 59a). It could be induced that this mitzvah also prohibits women from fighting in combat. Likewise, the men are told not to wear the (simlat) of a woman. This refers to the mantle. It was the mantle that differed between the men and women.

A common pagan practice was that men would wear women's clothing and women would wear men when they sacrifices to the image of Venus. Venus was know as Asherot to the people of Kena'an (Canaan). Maimonides (Moreh Nevochim, par. 3. c. 37) noted that it is commanded in the book of the Sabians, called Tomtom, that a man should wear women's clothing when he appears before the star of Venus, and the women should put on a coat of mail and armour when she stood before the star of Mars.

The Targum Yonathan (an Aramaic translation) says, "Neither fringed robes (tallit with the tzizit) nor tephillin which are the ornaments of a man shall be upon a woman." (See also Eruvin 96a; Orach Chaim 38:3). But there doesn't seem to be any distinction between men and women in the mitzvot of the tzitzit. However the mitzvah of k'li gever may suggest that there is a difference between a man's tallit and the women's tallit.

Speak to the children of Yisra'el, and bid those who they make them tzitziyot {fringes} in the borders of their garments throughout their generations, and that they put on the tzitzit {fringe} of each border a cord of blue:and it shall be to you for a tzitzit, {fringe} that you may look on it, and remember all the mitzvot {commandments} of YHVH, and do them; and that you not follow after your own heart and your own eyes, after which you use to play the prostitute (Bamidbar/Numbers 15:38-39).

Every man praying or prophesying, having his head covered, dishonors his head. But every woman praying or prophesying with her head unveiled dishonors her head. For it is one and the same thing as if she were shaved. For if a woman is not covered, let her also be shorn. But if it is shameful for a woman to be shorn or shaved, let her be covered. For a man indeed ought not to have his head covered, because he is the image and glory of YHVH, but the woman is the glory of the man. For man is not from woman, but woman from man;for neither was man created for the woman, but woman for the man. For this cause the woman ought to have authority on her head, because of the angels.Nevertheless, neither is the woman independent of the man, nor the man independent of the woman, in YHVH. For as woman came from man, so a man also comes through a woman; but all things are from Elohim. Judge for yourselves. Is it appropriate that a woman pray to YHVH unveiled? Doesn't even nature itself teach you that if a man has long hair, it is a dishonor to him? But if a woman has long hair, it is a glory to her, for her hair is given to her for a covering. (1 Corinthians 11:4-15)

Rav Sha'ul says that nature itself teaches us that the differences between men and women should be maintained.

Let your beauty be not just the outward adorning of braiding the hair, and of wearing jewels of gold, or of putting on fine clothing; but in the hidden person of the heart, in the incorruptible adornment of a gentle and quiet spirit, which is in the sight of YHVH very precious. For this is how the holy women before, who hoped in YHVH also adorned themselves, being in subjection to their own husbands: as Sarah obeyed Avraham, calling him lord, whose children you now are, if you do well, and are not put in fear by any terror. (1 Kefa/Peter 3:3-7)