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The reason given for the issur of beged ishah/beged ish is because it's a "toeivah" before Hashem (Devarim 22:5). The Gemara (Nazir 59a) learns from this that the issur is only for a man to dress up like a woman in order to mingle with women, or for a woman to dress like a man to mingle with men.

However, the Gemara in Makkos (20b) and Shabbos (94a) regarding plucking white hairs from amidst black ones seems to imply that one can violate lo silbash without having intent to mingle with the other gender - only that it's something that the other gender would do in terms of appearance. This also seems to be how the Gemara earlier in Nazir (39a) seems to hold, with regard to men shaving hair from underarms and beis ha'ervah.

My question is twofold. First, how is this contradiction resolved? Second, halacha l'ma'aseh, what do the poskim say about this? Do they pasken like the first Gemara, or do they say one may never dress like the other gender?

  • First, how is this contradiction resolved Why do you assume that there is some resolution, and that we are dealing with a contradiction? Maybe it is just two opinions. – mevaqesh Aug 21 '16 at 22:52
  • related judaism.stackexchange.com/a/38104/759 – Double AA Aug 21 '16 at 23:04
  • @mevaqesh Saying that it's a machlokes Amoraim is enough of a resolution for me. – DonielF Aug 22 '16 at 2:39
  • @DonielF okey dokey. – mevaqesh Aug 22 '16 at 3:00
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Halacha l'ma'aseh - If I remember correct, The Maharam of Padua in a responsum permits masquerading on Purim as a woman/man, giving the reason that it is only for the purpose of 'simchat Purim" and thus permitted. Others argue, see Hilchot Purim in Shulchan Aruch.

  • Related to your answer: judaism.stackexchange.com/q/14479. – Fred Aug 22 '16 at 17:46
  • Welcome to Mi Yodeya Chaco! Consider reading this Beginners' Guide to Mi Yodeya. Hope you choose to stick around the site. – mevaqesh Aug 22 '16 at 17:56
  • As Fred pointed out, that's a whole discussion in and of itself why Purim might be different. I'm asking if there's no reason other than you just feel like it if one is allowed to crossdress, and what that means in terms of the Gemaros I pointed out in my question. – DonielF Aug 22 '16 at 19:55
  • @DonielF Purim is Derabanan, so it can't fundamentally permit a Deorayta Lav. Must be certain kinds of crossdressing are permitted Deorayta (accd to this opinion), and this is one of them. – Double AA Aug 23 '16 at 4:25
  • @DoubleAA I suppose. But does that prove that we pasken like the Gemara in Nazir 59, or does it mean that we pasken that Beged Ishah is always assur, and for whatever reason Purim is an exception? – DonielF Aug 23 '16 at 4:55

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