Dressing up on Purim

Adapted from a shiur by Rav Avrohom
Yeshaya Cohen

Is it permitted for
a boy to dress as a girl on Purim or does this violate lo yilbash?
The Mahari Mintz allows for two reasons:

• Purim dress-up is done by both males and
  females, and is not done to appear like the other gender.
• We’re lenient for simchas Purim, just
  as gezel
  on Purim is not obligated to be returned.

The Darkei Moshe
then cites the Mahari Brin who argues with the second reason. If gezel relates
to beis din, who
is allowed to waive the obligation to return it; lo yilbash is issur v’heter, which
is not permitted just because of simchas Purim.

The first hetter is
not clear-cut either.

• Cross-dressing on Purim is often with
  intent to look like the opposite gender.
• Yad Haketana: Mahari Mintz himself may have been discussing
  masks, not clothing.
• Even if one’s intent is not to look like
  the other gender, many sources still indicate that it is assur:
  • Shulchan
    Aruch never mentions that
    intent matters.
  • Bach– Can’t cross-dress for simchas chassan
    either. The
    only hetter is
    if his intent has nothing to do with gender (e.g., he is cold).
  • Shach – Any hetter of intent applies only to a single article of
    clothing, but not total cross-dressing.

The practical
halacha is follows:

• Chayei Adam, Taz, Birkei Yosef, Shlah, etc. – Assur.
• Aruch HaShulchan – the minhag has been abolished.
• Pri Megadim/Mishna Berura — Efshar ein limchos (perhaps don’t need to protest) if only one begged is used, but not a whole outfit.
• Children
  • Sefer Purim Vchodesh Adar/ Minchas Yitzchak — Chazon Ish forbids kids also.
  • Igros Moshe (4:62) might allow in certain cases.