Question: Is it okay for a man to dress up as a woman and vice-versa on Purim?
Answer: The
Elya Rabba (696:15) suggests that the minhag of dressing up on Purim is
to commemorate Mordechai being dressed in royal clothing and escorted by Haman
(Esther 6:11).
The rishonim give different
reasons for the Torah prohibitions against crossdressing (Devarim 22:5). Rashi writes
that it can lead to promiscuity. Rambam (Moreh
Nevuchim 3:37; Mitzvos Lo Saaseh 39-40) explains that this was the way of
idolaters.
The Mahari Mintz (15) writes that
while cross-dressing is explicitly forbidden by the Torah, as one wears such
clothes on Purim to enhance one’s joy as opposed to immoral purposes, it is
allowed. He writes that he witnessed many such costumes and never saw the rabbanim
object. The Rema (OC 696:8) quotes both strict and lenient opinions, concluding
that the minhag is to be lenient.
Nonetheless, the Bach (YD 182)
quotes the Yereim (96) who writes that one must not even wear such clothes as a
joke at a wedding. His son-in-law, the Taz (YD 182:4) writes that while one can
follow the Rema, it is ideal to avoid doing so. The Mishna Berura (696:30)
quotes additional poskim (Kenesses Hagedola; Shelah) who condemned this
practice (see Aruch Hashulchan OC 696:12). R’ Ovadia Yosef (Yechave Daas 5:50) adds that one should
not even allow one’s children to cross-dress on Purim.
In conclusion, one should not cross-dress on Purim.
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