Two mitzvot involve the prohibition of transgender dressing. In the words of the Torah1:

a) "A man's attire shall not be on a woman,
b) "nor may a man wear a woman's garment,
"because whoever does these is an abomination to G‑d, your G‑d."

Cross-dressing can lead to promiscuous behavior.2 Wearing the clothes of a woman would enable a man to mingle inappropriately among women, and vice versa. In addition, for a man, simply putting on the clothes of a woman can lead him to have sinful thoughts.3

Maimonides, in his "Guide for the Perplexed,"4 states that some of the ancient pagan rituals involved cross-dressing and that we must therefore distance ourselves from this type of behavior.

Our Sages5 understood this prohibition to apply not just to clothing but also to certain cosmetic activities which are considered feminine in nature and may therefore not be practiced by men.

This article will focus on both the prohibitions regarding dressing and those regarding cosmetic practices.

Clothing

If there is a garment which is only worn by women, a man may not wear it. The same is true in the reverse.6

  1. A unisex garment which is worn either by men or women is permitted to be worn by those of either gender.7
  2. If it is a type of garment that has different styles for men and women — for example, a button-down shirt — a man may wear only the style that is for men, and a woman may wear only the style for women.8
  3. According to the Targum Yonatan ben Uziel on this verse, included in this prohibition is that a woman or girl may not wear a tallit or tefillin.9
  4. It is forbidden to even wear one garment of the opposite gender, even if the rest of the clothing the person is wearing is not of the opposite gender.10
  5. Some are lenient and allow an actor in a play to wear the clothes of the opposite gender, since the intention is not for promiscuity.11 The accepted opinion is that this is forbidden.12 If the actor wears only one garment of the opposite gender, one need not protest,13 although it is better to avoid even this.
  6. There are some halachic authorities who allow a woman to don the garment of a man (or vice versa) for the purpose of protection from the cold, and not in order to dress like a man.14 Others forbid this.15 Certainly, even in such a case, one may not clothe oneself completely in garments of the opposite gender.16
  7. Styles of dress vary in different locations and time periods, and it is only forbidden to wear the type of garment that is currently being worn in one's own location by members of the opposite gender. If the styles change and a particular garment becomes worn by both genders, it becomes halachically permissible. It is questionable as to whether this takes into account only the dress styles of the local (halachically observant) Jews, or also of the local non-Jews.17
  8. In light of this, and considering that it is commonplace for women in the Western world to wear pants, there are some opinions that pants are no longer considered a man's garment. Nevertheless, it is still considered immodest for women to wear pants as they are more form-revealing than a dress or skirt. (However, it is certainly better for a woman to wear pants that cover the entire leg rather than an immodest skirt or mini skirt.18) Many halachic authorities still consider pants to be a man's garment and therefore forbidden under the prohibition of wearing a man's garments as well.19
  9. Since it is normally only men who serve in combat units,20 it is forbidden for a woman to bear arms.21 It is for this reason that the righteous Yael killed the Canaanite general Sisra with a tent peg rather than a sword.22
    (Obviously, this rule is waived when needed for self-defense.)

Other Beautifications

Included in this prohibition is that a man may not beautify himself in ways that women ordinarily do. For this reason, men may not shave their armpits, legs or any body part which is normally shaved by women and not by men.23 The Tzemach Tzedek24 is of the opinion that it is therefore forbidden for a man to shave his beard, even with an acid cream, as this is considered the way of women (who remove facial hair if they have any). Others disagree.25

Since women generally try to appear young and often dye their hair to keep it from going gray or white, it is forbidden for a man to do so.26 A man may not even pluck out one white hair from amongst his black hairs.27 He may, however, dye his hair white.28

If a man's hair goes white prematurely and he wishes to dye his hair in order to be able to find a suitable match or a job, some authorities29 permit him to dye his hair.30