Answer: As early as 1322, Rav
Kalonymus ben Kalonymus
(Even Bochan, p30) writes about the minhag to dress up on Purim: And
on the fourteenth of Adar… one wears a woman’s dress, a necklace on his neck
and acts like one of the fools…
The Mahari Mintz (17) writes that while cross-dressing is
explicitly forbidden by the Torah (Devarim 22:5), 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, and says
that the minhag is to be lenient. Elsewhere (Darkei Moshe), the Rema
writes that some even allow one to wear a costume made of shaatnez on
Purim!
Nonetheless, the Mishna
Berura (696:30) quotes several Halachic authorities (Taz, Bach, Shelah, etc.)
who prohibit the practice. R’ Ovadia Yosef (Yechaveh
Daas 5:50) writes that one should not
even allow one’s children to cross-dress on Purim. Seemingly such costume was
far more prevalent in the olden days as the Aruch
Hashulchan (OC 696:12) writes that Jews no longer follow this practice.
While most
contemporary poskim forbid cross-dressing, we don’t need to criticize
those who do dress up in such a manner.
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