Cross-Dressing and Cross-Conduct: When Lo Yilbash Meets Contemporary Western Culture

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In recent decades, Western society has moved away from gender distinctions.[1] Many of these developments are ostensibly positive, such as equal pay for women and parental leave for men. Yet for halakhic and hashkafic reasons, other changes should give observant Jews reason to pause.

Before going forward, it is worthwhile clarifying that this piece does not aim to address questions about gender dysphoria, transgender, and non-binary identity in Halakhah. While many of the sources that we will explore can and have been used to inform such questions,[2] I will personally defer to poskim who possess both sensitivity and psychological expertise to address individuals who are struggling with these issues. This essay will instead focus primarily on the broader trend of dissolving gender norms within Western society. Two readily observable examples include the development of gender neutral attire and the acceptability of women serving in military combat units. As I will demonstrate, Halakhahhas much to say about these issues and broader questions of gender.

The Torah states: “A woman may not put on man’s apparel, nor shall a man wear (lo yilbash) woman’s clothing; for whoever does these things is abhorrent to the LORD your God” (Deuteronomy 22:5). Lest one think that the prohibition of Lo Yilbash is limited to literal crossdressing, R. Eliezer ben Yaakov, whose opinion is dispositive,[3] suggests that even certain forms of conduct can be classified as gender-specific:

R. Eliezer ben Yaakov says: How do we know that a woman should not go to war bearing arms? Scripture says, ‘A woman shall not wear that which pertaineth unto a man.’ [The words] ‘Neither shall a man put on a woman’s garment,’ [signify] that a man is not to use cosmetics [tikunei ishah] as women do. (Nazir 59a)[4]

The Talmud extends the prohibition of Lo Yilbash from the limited scope of crossdressing to encompass “feminine” activities such as certain types of grooming (see Makkot 20b) and “masculine” pursuits like warfare. Thus, it appears that Lo Yilbash is a very wide-reaching prohibition. The primary question we will reckon with is if and how it is applicable in a society that continues to erase any meaningful demarcation of gender norms.

Initially, we will make the case that Lo Yilbash is amorphous and relativistic, first on the individual level, and then from a societal standpoint. Subsequently, we will qualify this idea by exploring more demanding criteria for changing gender norms as well as categories that seemingly remain immutably gendered irrespective of the culture and times. Lastly, we will conclude by presenting the underlying philosophy behind Lo Yilbash to argue that the values it teaches us remain deeply relevant today.

The Purim Costume Controversy: Factoring in Alternative Intent

From a strictly halakhic standpoint, Lo Yilbash appears to have a degree of built-in flexibility, particularly in terms of the individual’s subjective state of mind.[5] Tosafot permit men to perform certain activities that the Talmud classifies as typically feminine, such as shaving armpit or pubic hair (Nazir 59a, s.v. ve-ha ka-gadil) or using a mirror (Avodah Zarah 29a, s.v. ha-mistaper), for pragmatic purposes. It presumably follows that they would permit wearing the opposite gender’s clothing for analogous intentions.[6] For instance, if a man has nothing to keep himself warm and borrows a woman’s coat to protect himself from the cold, he would not be violating Lo Yilbash. However, since an individual’s motives generally remain ambiguous to the observer, Tosafot conclude, “Only He [God] who discerns the hearts [of men] truly knows [this individual’s intent] (ibid).” Thus, the punitive enforcement of Lo Yilbash is often left to God, which, of course, does not detract from its severity.

The extent to which one’s alternative intent can serve to obviate Lo Yilbash is the subject of a classic debate between Mahari Mintz and Bayit Hadash regarding cross-dressing for Purim costumes: Mahari Mintz (Responsum no. 15) sought to justify the prevalent practice by drawing an analogy to Riva’s permission to commit theft on Purim, based on the principle of hefker beit din hefker (which empowers rabbinic authorities the right to determine the status of all property):

In any case, in our days, due to the joyous nature of Purim (mishum simhat Purim), it does not constitute theft, since he is not [stealing] to profit but in order to increase the joyous [playful nature] of Purim. So too here, in our case [of cross-dressing], he is not intending to commit promiscuity but rather to increase the joy of Purim.[7]

Bayit Hadash (Yoreh De’ah 182), however, polemicized this assertion as ludicrous for two reasons. Firstly, hefker beit din hefker only encompasses monetary matters; it cannot permit Lo Yilbash (the same way it cannot permit eating non-kosher food). Furthermore, and more important for our purposes, he writes that the consideration of alternative intent only applies in exigent circumstances:

Performing an act [of cross-dressing] is not analogous to one who is endeavoring to protect himself from distress. For even in a scenario in which one [cross-dresses] to save himself from distress, it is only permissible when there is no other option. However, there are many ways to bring joy to a groom and bride and to celebrate Purim without necessitating the violation of Lo Yilbash.[8]

Accordingly, alternative intent serves as a limited exemption to the prohibition of Lo Yilbash, which remains an overarching concern. Mahari Mintz, on the other hand, sees the absence of wrong intentions as rendering the act fundamentally permissible. This approach would significantly reduce the scope of Lo Yilbash and limit its practical applicability.

Does the Torah’s Standard of Gender Norms Change Based on Context?

The obviation of Lo Yilbash on the basis of a person’s alternative intent is, by definition, only an individual measure. To better understand whether Lo Yilbash is relativistic, we need to shift our focus to the societal level. As society changes, do the Torah’s standards for masculinity and femininity change with it? The answer to this question hinges upon how one interprets the following Talmudic passage: “A certain man was sentenced to scourging before R. Ammi, and when his armpits became bared, he noticed that they were not shaven. R. Ammi said to them: Let him go free. This man must be a member of the [learned] fraternity”(Nazir 59a).

The glaring question is why this individual deserved special treatment for not shaving his armpits – after all, are not all men forbidden from doing so due to the prohibition of Lo Yilbash? Rashba suggests that indeed all men are expected to adhere to this stricture, but alas, only the exceptionally pious were known to follow it. Rashba then proceeds to elucidate that widespread activity does not make the sin any more permissible: “And one who has become accustomed to a prohibited matter, and is drawn into it, and the masses are drawn into it, the prohibition does not become permissible. For if so, a person would persist in sinning, and [pious] individuals are more careful with this” (Responsa, 4:90). This is akin to the common motherly admonition, “If your friends jumped off the Empire State Building, would you do it too?” More people choosing to sin does not alter its prohibited nature.

However, Ran, in his commentary on Rif (Avodah Zarah 29a/b, s.v. Shomet et Yado), reaches the opposite conclusion: The prohibition of Lo Yilbash remains immutable like any other sin in the Torah, but the determination of what is considered to be masculine or feminine is subject to change. Thus, while the exceedingly pious continued to refrain from shaving their armpits, the masses were permitted to do so as the cultural line between masculine and feminine grooming had mostly shifted.[9]

Most authorities accept that the application of Lo Yilbash is subject to change; however, it remains unclear as to whom we look to assess these developments. Perishah (Yoreh De’ah 182:5) initially suggests that we observe what non-Jews wear and how they conduct themselves to determine what is considered masculine and feminine! Indeed, the consensus is that the practical application of Lo Yilbash is determined based on the cultural context.[10]

We thus return to our initial question: if all gender distinctions and norms are dissolved, would the Halakhah of Lo Yilbash become functionally inoperative?

The answer may depend on who is dissolving these norms. R. Moshe Shternbuch (Responsa Teshuvot Ve-Hanahgot 1:456), in determining whether women may smoke, cautions against basing the practical parameters of Lo Yilbash on general society. Instead, R. Shternbuch writes that we may only make inferences from those who are tzenuot (modest) in their conduct:

It would seem that we need to be concerned about a violation of Lo Yilbash. And even though, in the multitude of our sins, there are women who are found to do this, they are either non-Jews or secular individuals. Whereas the tzenuot safeguard their uniqueness and sanctity. A woman who breaks through the fence and conducts herself like those women whose primary intention is to emulate men, has violated the prohibition of Lo Yilbash, which is determined by the practice of modest women.[11]

Thus, while we may accept that the delineation of gender norms are subject to change, we must be careful as to whom we look for our cues. When God-fearing men began to use mirrors, or modest women began to drive cars, we can accept those developments as legitimate cultural change. However, when changes are promulgated by sectors of society that generally promote immodesty and promiscuity, the application of Lo Yilbash will remain unmoved.[12]

Tallit, Tefillin, and Weaponry: Inherently Gendered Activities?

While the line between masculine and feminine can shift based on the current culture, it is possible that Lo Yilbash is not as relativistic as we may be tempted to believe. Indeed, there is a basis to consider certain forms of dress and conduct as categorically gendered, and thus their prohibitive status would remain unyielding. To illustrate this point, we will focus on three case studies: tefillin, tzitzit, and weaponry.

The Talmud (Eruvin 96a) states: “Michal the daughter of the Kushite[13] wore tefillin and the Sages did not attempt to prevent her (v-lo mihu bah hakhamim).”[14] Many ask why Michal was permitted to wear tefillin, an article designated exclusively for men. R. Yechiel Ya’akov Weinberg (Responsa Seridei Eish 2:41:13) answers that since Michal simply did not intend to cross-dress, but instead wore the tefillin to fulfill a mitzvah, it was permissible.[15] Similarly, R. Yehuda Herzl Henkin (Responsa Benei Banim 2:3) permitted women to wear tzitzit under their regular garments: “If a woman’s sole intention is to perform a mitzvah, however, wearing a garment with tzitzit can be compared to wearing a man’s garment to protect against sun and rain.”[16] Rabbis Weinberg and Henkin both assume that tefillin and tzitzit, respectively,are no different than any other gender-specific garment.[17] Accordingly, the woman’s alternative intent (to fulfill a mitzvah) would be a legitimate basis to permit her wearing it.

However, there may also be a legitimate basis to claim that tefillin and tzitzit are “objectively” masculine and thus unequivocally forbidden for women to wear, thereby rendering the wearer’s alternative intent irrelevant. Targum Yonatan (pseudo-Jonathan) translates Deuteronomy 22:5 as follows: “Neither fringed robes nor tefillinwhich are the ornaments of a man shall be upon a woman; neither shall a man shave himself so as to appear like a woman; for every one who doeth so is an abomination before the Lord thy God.” By specifying tzitzit and tefillin, Targum Yonatan indicates that there is something uniquely prohibitive about them in nature. However, it remains unclear how and why they differ from other articles of clothing or activities.[18]

1) One suggestion, presented by R. Mordechai Carlebach in his halakhic essays on the parashah, (Havatzelet Ha-Sharon, Ki Seitzei, p. 342) is the counterintuitive nature in which a woman wearing tefillin and tzitzit would constitute cross-dressing. As noted above, Mahari Mintz propounded that any form of alternative intent, especially for the sake of performing a mitzvah, would be legitimate grounds to disregard concerns of violating Lo Yilbash. However, R. Carlebach points out that since tefillin and tzitzit are adornments specifically mandated by Halakhahfor men, a woman who intends to wear them to perform a mitzvah is not exempt from Lo Yilbash. For that very intention would be problematic since it is an article of clothing that the Torah designated for men! This assertion is diametrically opposed to Rabbis Weinberg and Henkin’s rationale that women may wear tefillin and tzitzit, respectively,for the purpose of fulfilling the mitzvah.[19]

2) A second suggestion is based on how Targum Yonatan interprets the prophetess Devorah’s recounting of the downfall of Sisera at the hands of Yael:

Her [left] hand reached for the tent pin, Her right for the workmen’s hammer. She struck Sisera, crushed his head, Smashed and pierced his temple. At her feet he sank, lay outstretched, At her feet he sank, lay still; Where he sank, there he lay—destroyed. (Judges 5:27-28)

Targum Yonatan (ad loc.) expounds that the reason Yael utilized a tent peg instead of standard weapon was “in order to fulfill that which is written in the Torah of Moses, that no form of a man’s weaponry should upon a woman,” alluding to the same position as R. Eliezer ben Yaakov, cited above. Despite the fact that Yael had alternative intent to neutralize a threat, she was nonetheless concerned with violating Lo Yilbash.[20] R. Carlebach (Ki Seitzei, p. 343-344) infers that alternative intent would be of no help here, since weapons are “inherently” maculine in nature and the pursuit of war is “given to men and not women” (masur le-ish ve-lo le-ishah). In other words, we need not concern ourselves with whether one intended to cross-dress for the sake of a mitzvah and whether that is a valid grounds for dispensation – for the Torah considers certain things intrinsically gendered regardless of the individual’s subjective state.[21]

R. Carlebach connects this argument back to the statement of R. Eliezer ben Yaakov cited in the beginning of this essay, suggesting that the very act of waging war is intrinsically masculine! Accordingly, the fact that some women serve in combat units today would be immaterial. While R. Moshe Feinstein did not think that women engaging in combat could be classified as violating Lo Yilbash, he nonetheless asserts, based on the Talmud (Kiddushin 2b), that “certainly women are not eligible members of battle (aval vadai ha-nishei lav b’nei milhamah ninhu)”(Igrot Moshe Orah Hayyim 4:75:3).[22] Thus, while typical clothing can perhaps shift depending on one’s cultural milieu, certain articles of dress and conduct might remain inextricably bound to a particular gender.[23]

Gender Norms as an Intrinsic Value

The halakhic and philosophical values of Lo Yilbash are more relevant today than, perhaps, ever before. Classically, most medieval theologians only presented two rationales for this prohibition. Rambam and Sefer Ha-Hinukh connect cross-dressing with licentiousness and idolatry.[24] Accordingly, Lo Yilbash seeks to either eradicate promiscuity, by ensuring that one cannot sneak their way into a gathering of the opposite gender,[25] or it is simply another measure to distinguish the Jews from their pagan neighbors.

While the opinion attributed to the (unnamed) Rabbis in Nazir 59a propounds the concern for promiscuity, R. Eliezer ben Yaakov, whose position is incorporated into later codes,[26] does not provide a rationale. It is difficult to read in the concern of idolatry, as it would not explain why R. Eliezer ben Yaakov singled out the specific examples of weaponry and grooming. Thus, we may argue that R. Eliezer ben Yaakov identifies something intrinsically and fundamentally problematic with the nature of breaking down the gender divide.

This necessity brings us to a third rationale for Lo Yilbash that, while less popular, fits far better with the accepted position of R. Eliezer ben Yaakov. The concern for Lo Yilbash, in the words of Ibn Ezra (Deut. 22:5), is simply “that God abominates the one who changes the works of the Lord.”[27] Abarbanel (Deut. 22:5) likewise states that “a man should be recognizable in his manliness and a woman in her femininity.” He further suggests that the Torah juxtaposes Lo Yilbash with the commandment to aid carrying a load because “it is appropriate for a man not to conduct himself like a woman and to refrain from lifting a heavy load to assist his brother. Rather, he should gird his loins and aid those who are in need.”

Centuries later, R. Samson Raphael Hirsch adopted the same understanding of the verse in his commentary on the Torah:

But according to R. Eliezar ben Yaakov, which is accepted as Halacha…a man is not to prink and prank himself in an effeminate manner. It seems that to us it is clear that, that according to this way of taking it the prohibition is not so much disguising one’s sex by dressing in female cloths as forbidding each sex that which is more specifically pertaining to the nature of the opposite one. A man is just as little to get himself up with powder and paint and lipstick etc. which is all quite well in order for a woman to do, and is in accordance with feminine nature, as a woman is to appear in a profession which belongs to the nature of men.[28]

Thus, we may suggest that R. Eliezar ben Yaakov provided the example of men grooming and women engaging in combat to convey that certain forms of conduct remain fundamentally masculine or feminine in nature regardless of how society develops.

This suggestion is not limited to the prohibition of Lo Yilbash but, indeed, is universal to the philosophy of the Torah. For instance, the Torah states, “You shall not round off the side-growth on your head, or destroy the side-growth of your beard” (Lev. 19:27). Rabbeinu Bechayei (Lev. 19:27) explains the reason men are prohibited from destroying their beards as follows: “The simple understanding is that it is forbidden to annul the sign that God impressed upon the males in order to distinguish them from their female counterparts. For one who does this [i.e. destroys their beard] has performed the antithesis of God’s work.”[29]

The aforementioned rabbinic commentators all make the same point: God created the world with intended norms and boundaries that He charges us to maintain. The following passage in the Talmud would seem to conclude with this very point:

Our Rabbis taught: It once happened that a man’s wife died and left a child to be suckled, and he could not afford to pay a wet-nurse, whereupon a miracle was performed for him and his teats opened like the two teats of a woman and he suckled his son. R. Joseph observed, Come and see how great was this man, that such a miracle was performed on his account! Said Abaye to him, On the contrary: how lowly was this man, that the order of the Creation was changed on his account! (Shabbat 53b)[30]

Lo Yilbash teaches us that God wishes for men to retain a baseline form of masculinity and women their femininity.

Granted, the definition of men’s and women’s clothing and conduct can change. While at one juncture it was exclusively masculine to wear pants, today it is not so.[31] There are few absolutely immutable categorical distinctions between how men and women must conduct themselves. As Deracheha, a woman’s Halakhah forum, aptly put it, “A woman seeking to dress like a woman need not dress in pinks and florals—unless they speak to her.” Similarly, it is acceptable in most circles for men to regularly use a mirror, unlike in Talmudic times.[32] I would add that neither are men required to completely repress their emotions to achieve the Torah’s standard of masculinity. Nonetheless, there remain a few impasses, such as women serving in military combat units, which are exceedingly difficult to justify in light of what we reviewed. Even if one could circumvent the halakhic challenges it is ostensibly at odds with the moral value that the prohibition of Lo Yilbash is meant to impart.

Regarding other professions, there is ostensibly nothing inherently problematic with a man who chooses to work as an RN or a woman who practices as an MD. If one does not do so to advance the negation of gender distinctions, but rather as a matter of pursuing their professional interest, it would not appear to conflict with the ethos of Lo Yilbash.[33] The yeshiva world’s kollel system would also necessitate such a distinction – for how else could one justify men studying while their wives assume the role of breadwinners?

Nonetheless, it is imperative to proactively maintain some form of gender marker. Many great rabbis[34] were sensitive to this broader moral necessity and were adamant about not even giving a child a name commonly used by the opposite gender. In a similar vein, R. Shmuel Wosner (Responsa Shevet Ha-Levi 9:175) rules that one must provide even prepubescent children with gender-distinctive clothing.[35] Reportedly, when R. Avraham Yeshaya Karelitz (Hazon Ish) saw one of his relatives dress his young daughter in pants for a Purim costume, he exclaimed, “ve-khi zeh hinukh? Is this how you educate your child?”[36] Indeed, we must ask ourselves what kind of values we seek to transmit and cultivate in our contemporary and future generations.

The imperative to maintain the integrity of gender norms remains more relevant today than ever, and it should encourage us to err to the side of caution in our observance of this Halakhah. While the details and applications of Lo Yilbash are debatable, the ethos is undeniable.

Midrash Tanhuma (Tazria, 5) relates that when Turnus Rufus challenged R. Akiva as to why God did not create baby boys pre-circumcised, the latter replied that “God gave the mitzvot to the Jewish people in order to refine them,” meaning that God wished to partner with humankind in the endeavor of perfecting His creation. One must be careful not to uproot God’s will from our world, but rather to accept His sacred charge to further enhance and build upon the foundation that He has created.

[1] Translations of Tanakh and Targum Yonatan on Humash are from; citations from the Talmud are from the Soncino edition; all other translations are my own unless otherwise indicated.
[2] See, e.g., recent works like Sefer Dor Tahapukhot, p. 53
[3] Yevamot 60a states, “mishnat Rabi Elazar ben Yaakov kav ve-naki,” meaning that while R. Elazar ben Yaakov was not prolific, his position is generally regarded as compelling. Kesef Mishnah (Laws of Idolatry 12:10) writes that Rambam ruled in accordance with R. Eliezer ben Yaakov based on this principle. See also Shulhan Arukh (Yoreh De’ah 182:5).
[4] Cf. Targum Onkelos, who interprets Deuteronomy 22:5 in a similar fashion. Aharonim, such as R. Moshe Feinstein (Igrot Moshe Orah Hayyim 6:75:3), note that R. Eliezer ben Yaakov’s statement can be read in an expansive way which emphasizes the entire enterprise of “go[ing] out to war” or, alternatively, in a more limited scope of “bearing arms” which would be limited to what the woman is wearing. Rambam (Laws of Idolatry 12:10) and Shulhan Arukh (Yoreh De’ah 182:5) cited above appear to take the latter approach. However, Sefer Bigdei Ish (p. 174) as well as other contemporary Rabbinic scholars have highlighted that R. Eliezer ben Yaakov may very well be concerned for gendered conduct.
[5] Bayit Hadash (Yoreh De’ah 182) uses this line of thinking to reconcile an apparent contradiction within Rambam’s Mishneh Torah, in which he writes that the prohibition of Lo Yilbash is only punishable rabbinically, while in the following Halakhah, he writes that one receives standard lashes for committing a Biblical violation (Laws of Idolatry 12:9-10). Bayit Hadash reconciles these conflicting rulings by suggesting that the latter case was punishable on a Biblical level due to the intent of crossdressing, whereas in the former case the man removed hair from his armpits and genitalia for the pragmatic purpose of achieving comfort (le-hasir ha-lihlukh ve-ha-mi’us). However, Kesef Mishnah (Laws of Idolatry 12:10) offers an alternative reconciliation by distinguishing between overt versus inscrutable violations of Lo Yilbash. Since armpits and genitalia are hidden under one’s clothing, it would only be subject to lashes on a rabbinical level. Cf. Beit Yosef (Yoreh De’ah 182), who elaborates on the same distinction of davar ha-nikar.
[6] However, Darkhei Teshuvah (Yoreh De’ah 182:9) cites Yad Ha-Ketanah, who prohibits cross-dressing regardless of one’s intentions. R. Moshe Feinstein (Responsa Igros Moshe Yoreh De’ah 182) explores whether the nature of Lo Yilbash hinges upon the act or result of cross-dressing. We might suggest that those who consider intention would more likely emphasize the deed while those who do not would focus on the result. However, while this suggestion works conceptually, it does not necessarily always play out in practice. See, e.g., Responsa Dor Reviei (no. 46).
[7] This rationale is codified by Rema (Orah Hayyim 696:8). However, Arukh Ha-Shulkhan (Orah Hayyim 696:12) writes, matter of factly, that while it was permissible in the Rema’s times, we no longer allow stealing or cross-dressing on Purim.
[8] See Taz (Yoreh De’ah 182:4) who promises blessings for all who follow Bah’s (his father-in-law’s) position – for such practices have led to many “stumbling blocks.” The Be’er HaGolah (Yoreh De’ah 182:7) adds that “many [evil] decrees and destructions have resulted from such practice.”
[9] This position is codified by Rema (Yoreh De’ah 156:2 and 182:1).
[10] Sefer Bigdei Ish (p. 242-243) points out that Halachah generally mandates us to distance ourselves from hukat akum, the ways of the pagans. It is thus surprising that in determining what is appropriate to wear vis-a-vis Lo Yilbash that we would be expected to violate this prohibition. However, it is possible to reconcile this should one adopt Rema’s (Yoreh De’ah 178) circumscribed understanding of hukat akum which limits it to promiscuous clothing.
[11] While R. Shternbuch is likely thinking of Haredi women, I believe it is reasonable to expand his principle to include other God-fearing Orthodox women within the category of tzenuot. However, while basing the standards of Lo Yilbash on tzenuot might be compelling in principle, it remains difficult to implement in practice since it is susceptible to the No True Scotsman Fallacy. Anytime a person or small group wishes to introduce change, they could easily be dismissed as not tzenuah due to breaking the communal norms.
[12] See Sha’arei Zevulun (no. 34) who similarly equates non-observant Jews with non-Jews for these purposes. Of course, individuals who cross-dress deliberately for ideological or frivolous purposes would not be subject to any of the leniences we reviewed, such as alternative intent, for their very motivation is to conduct themselves like the opposite gender.
[13] An epithet for King Saul.
[14] However, see Tosafos (Eruvin 96a, s.v. Michal) and Birkei Yosef (Yoreh De’ah 182:2) who cite an alternative text which records that the sages did indeed reprimand Michal for wearing tefillin.
[15] Alternatively, we might answer that opting not to protest is not tantamount to approval. Perhaps the Sages indeed did find Michals’ practice of wearing tefillin to be problematic, but for an external reason (e.g. fear of reprisal from her father, the king) they determined that it would be judicious to avoid confrontation.
[16] However, R. Henkin was not as flexible regarding a tallit gadol and tefillin. He writes: “A full-size men’s tallit is more problematic than a small arba kanfot, because the former is made for decorative purposes… she should [also] not lay tefillin, as the poskim conclude in Orah ayyim 38:3. Talmud Torah for women was permitted because it was necessary but tefillin are not necessary, and she should strengthen her ties to Judaism through other means.”
[17] See Responsa Maharam Shick (YOreh De’ah 173) who makes a passing remark which appears to concur with this point. However, it remains unclear whether this position is consonant with Bah‘s opinion that one may only cross-dress when there is no other recourse. On the one hand, there is no such thing as women’s tefillin, so this is the only way to fulfill the mitzvah. On the other hand, Michal had no necessity to wear tefillin to begin with. This point is further examined in Sefer Bigdei Ish (p. 123).
[18] While this passage in Targum Yonatan is not a typical halakhic source, and it is not cited by any rishon, as far as I am aware, several recent authorities discussed in this essay (e.g., Seridei Eish and Havatzelet Ha-Sharon) treat it as such. They also implicitly assume that the author of this text is the same one known as Targum Yonatan on Nevi’im and thus maintains the same position about Lo Yilbash indicated in his translation of Judges 5:27-28. However, Megillah 3a implies that Yonatan ben Uziel did not author a targum on Humash, and scholars generally regard that work attributed to him as pseudo-Jonathan.
[19] Alternatively, R. Carlebach cites Artzot Ha-Hayyim (No. 17), who suggests that Targum Yonatan espouses the minority position that prohibits cross-dressing regardless of one’s intentions. Accordingly, the woman’s intent to fulfill a mitzvah would not obviate the prohibition. This suggestion, however, would still not explain why Targum Yonatan singled out these specific activities over any other gendered ones.
[20] Targum Yonatan’s point fits well with the position of Bayit Hadash, who insists that even with permissible intentions one must utilize alternative methods to avoid running afoul of Lo Yilbash. According to Mahari Mintz, however, who more broadly allows cross-dressing in such cases, it is difficult to explain why Yael would have felt compelled to use a tent peg rather than a typical weapon.
[21] This assertion also finds support in a passage of Sefer Hassidim (no. 200) who writes that women who are in danger of being assaulted and raped may bear a sword due to the principle of eit le-asot le-Hashem hefaru toratekha – “It is a time to act for the LORD, for they have violated Your teaching” (Psalms 119:126). This rationale indicates that such behavior operates outside of the standard halakhic framework. Accordingly, a woman is fundamentally prohibited to bear a weapon regardless of her intent, perhaps, due to the inherently masculine nature of weaponry.
[22] Note, however, that both R. Feinstein and R. Ovadia Yosef (Responsa Yehaveh Da’at 5:55) permitted women to bear arms when it was necessary to anticipate the need for self-defense. Sefer Ha-Hinukh (no. 603) exempts women from the mitzvah of erasing Amalek and destroying the seven Cannanite nations (no. 604), since women may not wage war. However, Minchat Hinukh (604:3) questions this assertion on the basis of Sotah 44b, which states that even a bride must leave the wedding canopy for the war effort. Radvaz (Laws of Kings 7:4) resolves these conflicting assumptions by suggesting that while women do indeed join the war effort, they only do so in a supportive capacity by providing food and water for their husbands.
[23] See Bi’ur Ha-Gra (Yoreh De’ah 156:7) who indicates that conduct like grooming can be inherently feminine. Potentially, those who maintain such a position might suggest that Ran’s opinion noted above (that the definition of what constitutes masculine and feminine can change over time), provides a general rule, but it might not apply to specific examples of activities that the Torah would consider immutably gendered.
[24] Rambam, Sefer Ha-Mitzvot, Lav #40 (for further detail, see Guide 3:37:5); Sefer Ha-Hinukh (no. 542).
[25] See also the commentary of Abarbanel (Deut. 22:5).
[26] See above, note 2.
[27] Earlier in his commentary, Ibn Ezra also suggests that the rationale for Lo Yilbash is due to a concern for promiscuity. Cf. Ha-Emek Davar (Deut. 22:5).
[28] The Pentateuch Translated and Explained by Samson Raphael Hirsch, Vol. V Deuteronomy, trans. Isaac Levy, 2nd ed. (Gateshead: Judaica Press, 1976), Deut. 22:5. My thanks to R. Noah Marlowe for turning my attention to R. Hirsch’s comments on this verse.
[29] See The Prohibition of Shaving in the Torah and Halacha by Rabbi Dr. Zev Farber who makes extensive reference to Dr. Jacob Milgrom (A Continental Commentary, Lev. 19:27) to explain the historical significance of men’s hair: “In some ancient societies, including Israel, the beard was the prized symbol of manhood, and its mutilation was considered the greater disgrace and punishment (2 Sam. 10:4-5; Isa. 7:20). Among the Greeks, an old Spartan law forbids the aphori, from the moment of their taking office, to clip their beards; and those who fled before the enemy were forced to appear in public with half-shorn beards.” However, see Rambam in Mishneh Torah (Laws of Idolatry 12:1 and 12:7), who appears to understand this prohibition within the context of Lev. 19:26 and Lev. 19:28 which forbid practices such as divinations and tattoos which were a standard part of pagan rites. Cf. Ibn Ezra, Bekhor Shor and Seforno (Lev. 19:27). Note that when commentaries give divergent rationales for a mitzvah they are not necessarily to the exclusion of others – in our case, they may very well agree with Rabbeinu Bechayei’s interpretation.
[30] My interpretation of this passage is supported by Maharal (s.v. ve-ke’amar). However, other commentaries such as Maharasha and Iyun Yaakov (s.v. kamah) provide alternative rationales for the conflicting opinions presented in the Gemara.
[31] See Responsa Yabia Omer (Yoreh De’ah 6:14) for a less restrictive view and Responsa Minhat Yitzchak (2:108) for a prohibitive view.
[32] Rema (Yoreh De’ah 156:2); see Avodah Zarah (29a) and surrounding commentaries.
[33] It is worth noting that the hesitation to grant women serarah (positions of authority) can play a role in this discussion depending on how one interprets the Sifrei (Piska no. 157 on Deut. 17:15) and subsequent sources, such as: Mishneh Torah (Laws of Kings 1:5), Ramban (Shevuot 30a), Sefer Ha-Hinukh (Mitzvah no. 77), Tosafot (Bava Kamma 15a) and Igrot Moshe (Yoreh De’ah 2:44-45). A full analysis of this concept is beyond the scope of this paper.
[34] Responsa Divrei Malkiel (4:75).
[35] He bases this position on R. Yaakov Emden’s commentary on Tractate Shabbat (12a); Cf. Igrot Moshe (Even Ha-Ezer 4:62).
[36] Dinim V-Hanhagot Mi-Maran Hazon Ish (23:13).

Moshe Kurtz serves as the Assistant Rabbi of Congregation Agudath Sholom in Stamford, CT. His work focuses on examining contemporary issues such as political correctness, nationalism, and gender identity, through a halakhic lens. He also enjoys critically analyzing the relationship between Judaism and the sci-fi/fantasy genre, as well as heavy metal music. Moshe’s writings appear in The Journal of Halacha and Contemporary Society (RJJ Journal), Panim Journal, Tradition, The Lehrhaus, Torah Musings, and The Forward. To schedule a lecture or make an inquiry, please contact: