Cross Dressing in Halakha

(5) A woman must not put on man’s apparel, nor shall a man wear woman’s clothing; for whoever does these things is abhorrent to your God יהוה.

(1) (Devarim 22:5) "A man's vestment shall not be upon a woman": What does Scripture come to teach us? If that she should not wear colored clothing, is it not written (Ibid.) "for the abomination, etc."? And this is not an abomination. It means, rather, that a woman should not wear what a man wears and go among the men (for licentious purposes), and a man should not wear colored clothing and go among the women.

(2) R. Eliezer b. Yaakov says: Whence is it derived that a woman may not go out with armor to war? From "A man's vestment shall not be upon a woman." And whence is it derived that a man may not adorn himself with the adornments of women? From (Ibid.) "and a man shall not wear a woman's garment." For the abomination of the L-rd your G-d are all who do these"

(3) "It goes by five epithets: "cherem" (banned), "toevah" (abomination), "sanui (detested), "meshukatz" (revolting), "avel" (wrong).

(8) 8) (Vayikra 20:24) "I am the L–rd your G d, who separated you from the peoples.": See how different you are from the peoples. Among the idolators, a man decorates his wife and gives her to another; a woman decorates herself and gives herself to another!

§ Rav said: A person who is not a nazirite may lighten his burden by removing all the hair of his body with a razor. One who feels he has too much hair may shave all of it off with a razor, apart from his beard and the corners of his head. The Gemara raises an objection against this from a baraita: A man who removes the hair of the armpit or the pubic hair is flogged for transgressing the prohibition: “A man shall not put on a woman’s garment” (Deuteronomy 22:5), as this behavior is the manner of women. The Gemara answers: In this case he is flogged because he shaved with a razor, whereas in that case Rav said it is permitted because he was referring to one who removes hair with scissors, an act that is not considered a prohibition. The Gemara raises a difficulty: But Rav said it is permitted with a razor as well. The Gemara answers: He did not mean an actual razor; rather, he said that one may use an implement that is similar to a razor, i.e., scissors that cut very close to the skin, in the manner of a razor. Rabbi Ḥiyya bar Abba said that Rabbi Yoḥanan said: A man who removes the hair of the armpit or the pubic hair is flogged. The Gemara raises an objection against this ruling: The removal of hair is not prohibited by Torah law but by rabbinic law. Why, then, is he liable to receive lashes? The Gemara explains: What does it mean that Rabbi Yoḥanan says that he is flogged? This means that he is flogged by rabbinic law, a punishment known as lashes for rebelliousness, for disobeying a rabbinic decree. Some say a different version of this statement: Rabbi Ḥiyya bar Abba said that Rabbi Yoḥanan said: A man who removes the hair of the armpit or the pubic hair is flogged, due to the prohibition: “A man shall not put on a woman’s garment” (Deuteronomy 22:5). The Gemara raises an objection from a baraita: The removal of hair is not prohibited by Torah law but by rabbinic law. How then does Rabbi Yoḥanan say that he is flogged, which by definition is a punishment for individuals who have transgressed a Torah law? The Gemara answers: It was he who said this halakha in accordance with the opinion of that tanna, as it is taught in a baraita: A man who removes the hair of the armpit or the pubic hair violates the prohibition of: “A man shall not put on a woman’s garment.” The Gemara asks: And what does the first tanna, who holds that the prohibition is by rabbinic law, learn from this verse: “A man shall not put on a woman’s garment”? The Gemara answers: He requires it for that which is taught in the baraita, where it states: “A woman shall not wear that which pertains to a man, and a man shall not put on a woman’s garment, for whoever does these things is an abomination to the Lord your God” (Deuteronomy 22:5). What is the meaning when the verse states this? If it teaches only that a man may not put on a woman’s garment, and a woman may not wear a man’s garment, it is already stated in explanation of this prohibition that “it is an abomination to the Lord your God,” and there is no abomination here in the mere act of wearing a garment. Rather, it means that a man may not wear a woman’s garment and thereby go and sit among the women; and a woman may not wear a man’s garment and sit among the men. Rabbi Eliezer ben Ya’akov says: From where is it derived that a woman may not go out with weapons to war? The verse states: “A woman shall not wear that which pertains to a man, and a man shall not put on a woman’s garment,” which indicates that a man may not adorn himself with the cosmetics and ornaments of a woman, and similarly a woman may not go out with weapons to war, as those are for the use of males. Rabbi Yoḥanan’s ruling follows this opinion. § Rav Naḥman said: For a nazirite, it is permitted to shave armpit hair. The Gemara comments: And the halakha is not in accordance with his opinion. The Gemara reports that the Sages said to Rabbi Shimon bar Abba: We have observed that Rabbi Yoḥanan does not have armpit hairs, despite his own ruling that it is prohibited to shave them. He said to them: They fell out due to old age. The Gemara relates: There was a certain person who committed a transgression and was found liable to receive lashes before Rabbi Ami. When they removed his clothes to flog him, his armpit was exposed, and Rabbi Ami saw that he had not shaved his armpit hair. Rabbi Ami said to his attendants: Leave him; this is one of those who are meticulous in observance of mitzvot. We can see this is so, as he is particular about prohibitions that ordinary people do not observe. Rav raised a dilemma before Rabbi Ḥiyya: What is the halakha with regard to shaving armpit hair? He said to him: It is prohibited. Rav said to him: But it grows and is uncomfortable. Rabbi Ḥiyya said to him: Son of nobles [bar paḥtei], this hair has a limited time. Whenever a hair grows too long it falls out, and therefore there is no concern that one’s armpit hair will become too long. Rav raised another dilemma before Rabbi Ḥiyya: What is the halakha with regard to rubbing armpit hair and thereby removing it manually? Rabbi Ḥiyya said to him: It is prohibited. Rav continued to ask: What is the halakha with regard to rubbing armpit hair indirectly with one’s garment? Rabbi Ḥiyya said to him: It is permitted. Some say that this was not Rav’s question; rather, he raised the following dilemma before him: What is the halakha with regard to rubbing the armpit with one’s garment during prayer? Rabbi Ḥiyya said to him: It is prohibited. The Gemara comments: And the halakha is not in accordance with his opinion in this case.

(1) If you see your fellow Israelite’s ox or sheep gone astray, do not ignore it; you must take it back to your peer. (2) If your fellow Israelite does not live near you or you do not know who [the owner] is, you shall bring it home and it shall remain with you until your peer claims it; then you shall give it back. (3) You shall do the same with that person’s ass; you shall do the same with that person’s garment; and so too shall you do with anything that your fellow Israelite loses and you find: you must not remain indifferent. (4) If you see your fellow Israelite’s ass or ox fallen on the road, do not ignore it; you must raise it together. (5) A woman must not put on man’s apparel, nor shall a man wear woman’s clothing; for whoever does these things is abhorrent to your God יהוה. (6) If, along the road, you chance upon a bird’s nest, in any tree or on the ground, with fledglings or eggs and the mother sitting over the fledglings or on the eggs, do not take the mother together with her young. (7) Let the mother go, and take only the young, in order that you may fare well and have a long life. (8) When you build a new house, you shall make a parapet for your roof, so that you do not bring bloodguilt on your house if anyone should fall from it. (9) You shall not sow your vineyard with a second kind of seed, else the crop—from the seed you have sown—and the yield of the vineyard may not be used. (10) You shall not plow with an ox and an ass together. (11) You shall not wear cloth combining wool and linen. (12) You shall make tassels on the four corners of the garment with which you cover yourself.

(1) A WOMAN SHALL NOT WEAR THAT WHICH PERTAINETH UNTO A MAN. This law was stated here because Scripture deals with going out to war. Women were created only to have children.. If a woman joins men in going to war she will come to engage in illicit sexual relations on the way.The law that states neither shall a man put on a woman’s garment is similar.The reason for this law is as follows. If a male who does not have a full beard. mixes with women, then he and they will have sexual relations without anyone knowing. This law indicates that the custom of Israel was for the garments of men to be unlike the garments of women. There was a definite difference between the garments. This is also the practice in most countries. Some say that our verse speaks of unnatural intercourse. However, there is no need for this interpretation. The fact is that God abominates the one who changes the works of the Lord.

(1) That a woman should not wear the adornments of a man: That women should not wear the clothing of men and not arm themselves with their weapons. And about this it states (Deuteronomy 22:5), “There shall not be the vessel of a man upon a woman.” And Onkelos translated [it], “There shall not be a weapon of a man upon a woman.” (See Nazir 59a.)...

(2) It is from the roots of the commandment [that it is] to distance our holy nation from matters of sexual immorality and any matter and any angle whatsoever that contains a stumbling block towards it — as the matter that they, may their memory be blessed, said metaphorically (Sanhedrin 106a) that our God hates promiscuity. [This] means to say, that in His love for us, He distanced us from promiscuity, which is an exceedingly ugly thing, [and which] takes the heart of a man and pushes it off from the good path and from desirable thoughts, to a bad path and thoughts of stupidity. And there is no doubt that if the clothes of men and women were the same, they would constantly mix — these with those — “and the world would be filled with promiscuity.” And they also said in explaining this commandment that it is to distance all matters of idolatry, as the way of the worshipers of idolatry was with this. And I found these two reasons in the books of Rambam (Sefer HaMitzvot, Negative Commandments 40; Guide for the Perplexed 3:37) after I wrote them.

(1) That He prohibited us from being drawn to the practices of the idolaters, such that women wear mens' clothes and adorn themselves with their ornaments...

(1) That He prohibited us from men adorning themselves with women's ornaments. And that is His saying, "nor may a man wear a woman’s garment" (Deuteronomy 22:5). And any man who adorns himself like this or wears what is well-known in that city to be an ornament specific to women - is lashed.

And you should know that this procedure - meaning that the women adorn themselves with men's ornaments and the men adorn themselves with women's ornaments - is done to arouse the drive for promiscuity, as is explained in the books written about this. And it is often placed in the stipulations for the making of some talismans and said, "If a man is occupied with it, he should wear women's garments and adorn himself with gold and pearls and that which is similar to them; but if it was a woman, she should wear armor and arm herself with swords." And this is very famous among those of this opinion. (See Parashat Ki Tetzei; Mishneh Torah, Foreign Worship and Customs of the Nations 11.)

(9) The Torah does not forbid the removal of hair from other portions of the body e.g., the armpits or the genitalia. This is, however, prohibited by the Rabbis. A man who removes [such hair] is given stripes for rebelliousness.
Where does the above apply? In places where it is customary only for women to remove such hair, so that one will not beautify himself as women do. In places where it is customary for both men and women to remove such hair, one is not given stripes. It is permitted to remove hair from our other limbs with scissors in all communities.

(10) A woman should not adorn herself as a man does - e.g., she may not place a turban or a hat on her head or wear armor or the like. She may not cut [the hair of] her head as men do. i.e., a woman's coiffure may not resemble a man's. The Yemenite manuscripts of the Mishneh Torah read יגלה, "reveal," instead of יגלח, "cut." According to that version, the Rambam is saying that when a woman goes out without covering her head, in addition to violating the basic laws of modesty (see Hilchot Ishut 24:11-12; Hilchot Issurei Bi'ah 21:17), she is also transgressing this Torah prohibition.
A man should not adorn himself as a woman does - e.g., he should not wear colored garments or golden bracelets in a place where such garments and such bracelets are worn only by women. Everything follows local custom.
A man who adorns himself as a woman does, and a woman who adorns herself as a man does, are [liable for] lashes. When a man removes white hairs from among the dark hairs of his head or beard, he should be lashed as soon as he removes a single hair, because he has beautified himself as a woman does. Similarly, if he dyes his hair dark, he is given lashes after dyeing a single hair.
A tumtum and an androgynous. may not wrap their heads [in a veil] as women do, or cut [the hair of] their head as men do.11...
According to the Yemenite manuscripts mentioned above which substitute יגלה, "reveal," for יגלח, "cut," this clause also must be amended accordingly. If they do [either of the above], they are not [liable for] lashes.

Because of his pain - If the only pain that he suffers is that he is embarrassed to walk among people then it is permissible, because there is no greater pain than this.

One may not look into a mirror on the Sabbath. If it was fixed on a wall, Rebbi permits and the Sages prohibit. Rebbi Aḥa in the name of Rebbi Abba: The reason of him who forbids that occasionally she will see a white hair and tear it out which brings her to the obligation of a purification sacrifice But for a man it is forbidden also on weekdays because it is not honorable. Three things they permitted the House of Rebbi, that they might look into a mirror, that they got a haircut with a lock and that they taught their children Greek, because they were in need of Roman government connections.

An Israelite may get a haircut from an idol worshiper (if) he can see in a mirror. (If) from a Samaritan, he does not need to look in a mirror. The house of Rabban Gamaliel permitted one to look in the mirror because they are in contact with the government. An Israelite who cuts the hair of idol worshiper, when he reaches the forelock, he should remove his hand..

(8) One may marry a woman on Purim, RMI: both on the fourteenth and on the fifteenth. All the more so, one may redeem one's firstborn (Tosfot to ch. 1 of Moed Qatan). The custom of wearing masks on Purim, and of crossdressing, is totally permitted because of its innocent and joyful purpose, as is the wearing of shaatnez. While some would prohibit it, our practice is as I have already said. So too those who playfully rob each other do not violate "Thou shalt not steal'', and such is our custom. However, you may do only as local elders permit. (Responsum of MHRI Minz #17).