Cross Dressing

The Torah commands us (Deut. 22:5) "A woman shall not wear that which pertains to a man, neither shall a man put on a woman's garment; for whoever does these things is an abomination unto the Lord your God." Effectively, this means, among other things derived from this verse, that a man may not dress like a woman and vice versa.

There are two major disagreements regarding the details of these prohibitions that have practical ramifications.

I. Non-Mischievous Dressing

The Semak (33) writes that the reason for these prohibitions is that a man or woman will dress like the opposite gender in order to enable immoral relations. The Semag (Lavin 59-60) seems to say that as well, albeit somewhat vaguely. (The Binas Adam (90) reads the Semag differently, although I really don't see it in the text.) This would mean that it would be permissible for a man to dress like a woman as a joke. And so the Mahari Mintz writes in a responsum (15) regarding wearing costumes of the opposite gender on Purim. Significantly, the Rema (Shulchan Arukh, Orach Chaim 696:8) rules according to the Mahari Mintz.

However, there is no indication for such a leniency in the Rambam's Mishneh Torah (Hilkhos Avodah Zarah 12:10) and the Birkei Yosef (Shiyurei Berakhah, Orach Chaim 696:3) quotes a responsum from the Rambam in which he explicitly prohibits dressing like the opposite gender as a joke at a wedding (others, such as R. Nachum Rabinovitch in his Yad Peshutah ad loc., attribute this to R. Avraham ben Ha-Rambam). Similarly, the Yere'im (96) rules that a man may not wear women's clothes as a joke, even at a wedding.

Based on this Yere'im, the Bach (Yoreh De'ah 182) argues on the Rema's leniency for Purim. However, the Bach still permitted wearing women's clothes if one's intent is not to look like a woman, e.g. if it is raining and the only raincoat available is a woman's. However, the Shakh (Yoreh De'ah 182:7) attempted to bridge these two positions. He suggested that wearing some women's garments, but not looking entirely like a woman, is allowed for a joke. But dressing exactly like a woman to the point of looking like one is always prohibited. Thus, the Yere'im must have been speaking about doing the latter at a wedding, which is prohibited, while the Rema was speaking about the former on Purim, which is permitted. The Pri Megadim (Orach Chaim 696: ) seems to rule like this Shakh.

This leads to the second area of disagreement.

II. One or Multiple Articles of Clothing

Is the prohibition to only wear one article of clothing from the opposite gender or to dress entirely? If the latter, it would be entirely permissible for a man to put on a woman's scarf as long as he is wearing pants. The aformentioned Shakh accepts a leniency if one is wearing only some garments from the opposite gender. The Bach goes even further and suggests that it is entirely permissible if one is not fully dressed like the opposite gender. However, this is difficult because it is not mentioned in the rishonim. To the opposite, the Rambam seems to say that it is prohibited to wear even one article of clothing, without making any distinctions. The Revid Ha-Zahav (Ki Setze, sv. lo silbash) makes the observation that the verse prohibits a woman from wearing a keli gever, an article of clothing, in the singular. And so the Rema (Yoreh De'ah 182:5) ruled.

III. On Purim

As mentioned above, the Rema allows dressing like the opposite gender as part of a Purim celebration. However, the Bach strongly attacks this view. His son-in-law, the Taz (Yoreh De'ah 182:4), ruled that technically one can follow the Rema but one who is stringent is praiseworthy. The Shakh and Pri Megadim defended the Rema's position, while the Birkei Yosef opposed it. The Mishnah Berurah (696:30) quotes the Shela"h, Be'er Ha-Golah and Kenesses Ha-Gedolah who warned against following the practice. Significantly, the Arukh Ha-Shulchan (696:18) wrote that the Rema's justification did not apply in his (the Arukh Ha-Shulchan's) time because the practice was not to dress like that.