Cross Dressing in Jewish Law

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Deuteronomy 22:5

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 G!d HaShem.

לֹא־יִהְיֶ֤ה כְלִי־גֶ֙בֶר֙ עַל־אִשָּׁ֔ה וְלֹא־יִלְבַּ֥שׁ גֶּ֖בֶר שִׂמְלַ֣ת אִשָּׁ֑ה כִּ֧י תוֹעֲבַ֛ת HaShem אֱלֹהֶ֖יךָ כׇּל־עֹ֥שֵׂה אֵֽלֶּה׃


But why would the Torah say this??


The Gemara asks: What do we learn from “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 HaShem your G!d,” and there is no abomination here in the mere act of wearing a garment.

וְתַנָּא קַמָּא הַאי לֹא יִלְבַּשׁ גֶּבֶר מַאי דָּרֵישׁ בֵּיהּ מִיבְּעֵי לֵיהּ לְכִדְתַנְיָא לֹא יִהְיֶה כְלִי גֶבֶר עַל אִשָּׁה מַאי תַּלְמוּד לוֹמַר אִם שֶׁלֹּא יִלְבַּשׁ אִישׁ שִׂמְלַת אִשָּׁה וְאִשָּׁה שִׂמְלַת אִישׁ הֲרֵי כְּבָר נֶאֱמַר תּוֹעֵבָה הִיא וְאֵין כָּאן תּוֹעֵבָה


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.

רַבִּי אֱלִיעֶזֶר בֶּן יַעֲקֹב אוֹמֵר מִנַּיִן שֶׁלֹּא תֵּצֵא אִשָּׁה בִּכְלֵי זַיִין לְמִלְחָמָה תַּלְמוּד לוֹמַר לֹא יִהְיֶה כְלִי גֶבֶר עַל אִשָּׁה וְלֹא יִלְבַּשׁ גֶּבֶר שִׂמְלַת אִשָּׁה שֶׁלֹּא יִתַּקֵּן אִישׁ בְּתִיקּוּנֵי אִשָּׁה


More recently…

Sefer Chasidim 702, 206 - Written by Judah HeHasid (c.1140 - c.1200 CE)

While travelling, a woman heard that a group of gentiles was approaching. She feared that

they might rape her. Under such circumstances, she is permitted to dress as a nun so that they will believe that she is a nun and not rape her. If she learns that Jewish robbers are approaching, she is likewise allowed to dress in the style of the gentiles and claim that

she is a gentile. She is permitted to threaten that she will cry out and report them [to the

authorities]. She is permitted to scream for help right away so that gentiles will come and save her, even if the gentiles will kill the [ Jewish] attackers. 


The Torah states: ‘A woman shall not put on a man’s apparel, nor shall a man wear a woman’s garment’ (Deut. 22:5). Nevertheless, if an enemy army is laying siege to a city, or if, on the road, the enemies would find out that they are women, and then they would rape them, the women they should put on men’s clothing and even carry swords in order to make them think that they are men. And if twenty [non-Jewish] men should come, and there are only ten [ Jewish] men and about forty women, the women should all gird themselves with swords to make them [= the non-Jews] think that they are men and thus not harm them. 


Shulchan Aruch, Orach Chaim 696:8- 16th Century

As to the custom of wearing 'faces' on Purim, and men who wear women's dresses and women wearing men's attire - this is not forbidden, for they have no intention other than pure pleasure. 

מה שנהגו ללבוש פרצופים בפורים וגבר לובש שמלת אשה ואשה כלי גבר אין איסור בדבר מאחר שאין מכוונין אלא לשמחה בעלמא


Sermon by Rabbi Lisa Edwards

I have long been fascinated by this verse (Deuteronomy 22:5) . . .Perhaps because, ever since I was a little kid, my mom let me, even helped me, dress most of the time “like a boy,” and keep my hair short even in an era when every other little girl had long hair. I dressed, as I said, “like a boy,” but that’s a phrase really that other people would use, not me, and not my mother, who would sometimes counter their remarks with something like, “no, she dresses like herself”. . .


Understanding Transgender Issues in Jewish Ethics- Sermon by Rabbi David Teutsch, Ph.D.

The Talmud says that what is prohibited is falsifying identity for the purpose of spying on the other sex. The great medieval commentator Rashi says that the prohibition is limited to concealing identity for the purpose of adultery. The Shulhan Arukh notes that cross-dressing is permitted on Purim because its purpose is simha (celebration, joy) and that it is forbidden if it is for the purpose of fraud. In limiting the prohibition to situations of fraud and deception, the talmudic and medieval rabbis indicated that cross-dressing in a way that is true to the cross-dresser’s identity is permitted.