A man's item shall not be on a woman, and a man shall not wear a woman's
garment; whoever does such a thing is an abhorrence unto Adonai.
It starts at birth: The girl gets the pink blanket, the boy gets the blue. What is the first thing people say when a baby is born? "Is it a boy or a girl?"
In popular culture, gender ambiguity is a point of discomfort, to say the least. Any miscue is considered either funny or offensive, any crossover at best avant garde and at worst degenerative or subversive. Many viewers of films such as "The Crying Game" and "The Birdcage" see crossdressers as either laughable or pathetic, or both. Generally speaking, gender clues have been incorporated into clothing style, even for infants, in order to prevent misidentification.
And so it would seem at first glance that our Torah holds such a concern, as our verse from Deuteronomy seems to prohibit "crossdressing." Let's look at the passage and how it has been interpreted by our sages.
There are three clauses in this passage.
(1) A man's item shall not be on a woman;
Note the lack of parallel structure in the first two clauses. We might have expected the verse to say, "(1') A man may not wear women's clothes; (2') and a woman may not wear men's clothes." It is no violation of Biblical Hebrew style to repeat the same words in a single sentence, so it is peculiar that we do not have matching phrases. The words "man's" and "men" come first in both clauses, and in order to allow that, the first clause is passive while the second is active. Moreover, the first clause talks of kli gever "items" or "appurtenances" while the second clause used the word simlat "dress" or "garment." It seems that the verse speaks of two differing but related rules.
Nonetheless, some of our sages read these two clauses as if they were the statement of a two identical rules, one applying to men, one applying to women. That is, they read it as if it says, "a man or a woman shall not wear the items of the other gender." But most sages treat the two verses as distinct in intent.
One of the most unusual interpretations is that of the early Aramaic source referred to as Pseudo-Yonatan, a translation of the Hebrew Bible that renders kli gever, "a man's items" as tsitsit (tallit or prayer shawl) and tefillin (phylacteries or prayer amulets worn by traditionally observant Jews). Since these items are required by halakha (Jewish law) for men but not for women, they are quintessential "men's items" and thus are the subject of this law, suggests Pseudo-Yonatan.
A debate has been raging for the past two-thousand years over whether women may wear tallit and tefillin, and if so, which berakha (blessing) they say when putting them on. In the course of that debate the minority who forbid women from wearing tallit and tefillin do not cite this interpretation or this verse as proof of their position. Moreover, none of the mainstream halakhic (legal) interpretations of this verse follow the midrash of Pseudo-Yonatan. Thus, this interpretation, while interesting, has no legal weight.
In another attempt to identify the quintessential "men's items," Rabbi Eliezer ben Jacob, quoted in the Talmud (edited about 800 C.E.), says, "What is the proof that a woman may not go forth with weapons to war?" He then cites our verse, which he reads this way: "A warrior's gear may not be put on a woman" (B. Naz. 59a). He reads kli gever as the homograph kli gibbor, meaning a "warrior's gear."
This same understanding is followed by Midrash Mishlei (Proverbs) which contends that the Biblical character Yael in the Book of Judges kills General Sisera with a tent pin instead of a sword in order to comply with this law. It would have been "unlady-like" for her to use a sword -- worse, a violation of the law -- because a sword is a man's tool and so the righteous woman of valor finds an alternate weapon.
While this interpretation does not prevail in later halakhic discussion, it does appear, and so it must be regarded as a viable albeit minority view as to the intent of the first clause. This interpretation has even been cited in the debate over exemption for women from military conscription in modern Israel.
A common understanding of our verse in exegetical and halakhic literature is stated by Rashi, one of the most highly-regarded Talmudists and Biblical commentators of all time (c. 1100 C.E.): "Kli gever, a man's item should not be on a woman: That she should not appear as a man so she can go out among men, for this is only for the purpose of adultery."
Likewise, Rashi says, "Simlat Isha, a man shall not wear a women's garment: So he can go and be among the women."
Rashi explains the moral force of this: "To`eva, abhorrence: The Torah forbids only garments that may lead to to`eva, abhorrence." This comment appears in Rashi's Torah commentary, so it is not clear whether Rashi is defining the reason for the law or, alternatively, its scope.
Only a few sources spell out what is meant by "women's clothing" and "men's clothing." Women normally wear colorful clothes; men wear white. Most sources leave the particulars undefined, because they realized that while gender distinction in dress is almost universal, the particulars are a matter of local fashion trends. As the Tur (about 1300 C.E.), the predecessor code of the Shulhan Arukh, puts it: "A woman should not dress in clothes specifically for men lefi minhag hamaqom according to the local fashion" (YD 182).
The intent of the law, in this view, is to prevent men and women from associating with what would normally be a single-sex group of the other gender under false pretenses for purposes of, or circumstances that are liable to lead to, heterosexual adultery. Rashi seems to limit the prohibition to this case. Thus men and women cross-dressing in other circumstances might not be prohibited, at least if it can be assured that the "abhorrence" will not result.
This is the analysis followed by the Shulhan Arukh, the 16th century law code that has become a standard law text for most of the traditionally observant Jewish people. In its discussion of the laws of the festival of Purim, the Code says men and women may cross dress on Purim because it is for the purpose of gaity (simha), not for adultery. Given the context, there is no danger that such cross-dressing will lead to heterosexual adultery.
The danger of "cross-dressing," according to the analysis followed here by Rashi and the Shulhan Arukh, is that it might allow men to enter women's groups and women to enter men's groups. In societies in which gender segregation was widely observed, this subterfuge was seen as a real danger. This was even before the production of "Yentl."
It is stated this way in Sefer HaHinukh: "The root of this mitzva (commandment) is to keep us from sexual sin...and there is no doubt that if men and women's clothing were the same, they would mix and the earth would be filled with impropriety" (sec. 564).
Today the concern would be that men or women would sneak into the other gender's locker rooms or bath rooms. Given that men and women in our society mix freely in other settings, it is hard to see how heterosexual adultery is a particular danger of what is called "cross dressing."
Some commentators have noted, however, that this understanding as explained by Rashi and the Shulhan Arukh does not seem to be based on the language of the verse. If the Torah had wanted to prohibit men from going out among women in women's dress it could have said that. This context of social mixing of men and women is imposed on the verse.
A second interpretation of the verse has gained the widest acceptance among the sages as reflected in mainstream legal codes. The Shulhan Arukh (Yore De`a) says that the prohibition of a man wearing simlat isha "woman's dress" refers to wearing a women's hairstyle, which, depending on local custom, means specifically to shave hair from one's underarms or genital region. Men may not shave their armpits and genital regions as women do unless it is customary locally for men to do that. Men may however shave arm & leg hair in any case.
Other commentators likewise relate the simlat isha clause only to removing underarm and pubic hair.
This interpretation may seem far from the apparent intent of the verse in Deuteronomy. In part, that is because the legal sections of the Torah use terms that have technical meaning to those well-versed in Biblical law. In addition, the history of legal interpretation in Jewish law is not unlike that of other legal systems in that judges ultimately must apply the laws to real-life situations and are thus forced to define the terms in a way that will make sense within the framework of their codes, case law and social reality.
It appears that the scope of this law as interpreted by our sages is limited. It is designed especially to prohibit men and women from misrepresenting themselves as the other gender with the aim of illicit heterosexual activity. The mitzva does not prohibit cross dressing for the festival of Purim. It also would probably not prohibit cross-dressing in a private setting or for theatrical purposes, nor would it prohibit such dress when it would not mislead others as to the gender of the person under the clothes.
The third clause of the verse, "whoever does such a thing is an abhorrence unto Adonai," has been understood by our sages to mean that it is the forbidden act that is an abhorrence, not the person. The wording of this clause is merely a figure of speech, an idiomatic usage, and should not be taken to refer to the person himself or herself.
The Torah's concern in this verse, then, is not with creating or reinforcing gender differences per se, but in preventing gender associations of clothing or possibly body hair from being used to deceive others for purposes leading to sexual immorality. The key here seems to be deception for illicit purposes. Indeed this law appears in Deuteronomy in the context of laws against deceit.
In American society the fashion trend over the past decades seems to be toward a larger body of "unisex" apparel. At the movie theatre the teenage women selling popcorn are wearing suits and ties. Jeans are common to all genders as are sweaters and jackets. It is much more common for genuine intentional transvestites to be accepted publicly. A person's gender can less easily be judged by their clothing, and many people like it that way.
While the legal interpretations of this verse from Deuteronomy have been diverse, most of Jewish legal discussion has not taken the verse to suggest a blanket ban or condemnation of what today we call "cross dressing."
This discussion is meant to be informational only, not determinative of Jewish law for this verse or the issue of cross dressing generally. Persons of the Jewish faith should abide by the legal interpretation of the verse as it is understood by their local community as explained by their rabbi. This discussion does not make any claim for the permissibility or restriction on cross dressing based on other Biblical and post-Biblical (Rabbinic) legislation.
If you would like to learn more of what the Torah teaches on this and other subjects, go and study.