May children dress themselves with clothing of the opposite gender?
Children who have reached the age of Chinuch must be educated not to dress in clothing of the opposite gender [unless there is no other clothing available and they need to wear it to protect from the cold or the sun]. Some write this begins from age six. Other’s write this begins from age three. Other Poskim rule the obligation to educate the child begins from the age in which the child or/and parents are embarrassed for him/her to wear clothing of the opposite gender.
May one dress children under the age of Chinuch in clothing of the opposite gender?
Some Poskim rule that children of all ages, even below Chinuch and even a baby, may not have clothing of the opposite gender placed on them [unless there is no other clothing available and they need to wear it to protect from the cold or the sun]. Other Poskim however rule one may dress children in opposite gender clothing until the child is of age that he/she or the parents are embarrassed for him/her to wear clothing of the opposite gender.
May one place a Yarmulke on a baby daughter’s head? This is subject to the same dispute as cross dressing for the sake of jest and fun, explained above, and to whether the prohibition applies to children below the age of Chinuch/embarrassment.
May children cross dress for a skit, play and the other purposes of the like?
No. However, if he/she remains recognizable as a man/woman and merely wears a single clothing of the opposite gender, there is room to be lenient. Many however are stringent in all cases, and the Rebbe expressed contempt for children who cross-dress for school plays and the like.
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 Meaning that they are getting dressed themselves, regarding if they may be dressed by an adult-see next Q&A!
 Shevet Halevi 6/118-4
 See Ohel Yaakov p. 291
 See Ohel Yaakov ibid footnote 33 in name of Rav Elyashiv
 Igros Moshe E.H. 4/62-4
 Minchas Yitzchak 2/108; Kerem Shlomo 17-3; Minchas Peri 2/66; Poskim brought in Ohel Yaakov 292
 See Minchas Yitzchak ibid
The reason: As it is forbidden for an adult to dress even a child with men’s clothing as it is forbidden to feed a prohibition to a child of any age. [Minchas Yitzchak ibid, based on Admur 343/2]
 Igros Moshe E.H. 4/62-4
 Shevet Hakehasi 2/258; Mishneh Halachos 7/43; Ohel Yaakov p. 288
The reason: This matter is subject to the same dispute mentioned regarding cross-dressing on Purim or for a wedding, in which we concluded like the stringent opinion. Furthermore, there is room to learn that in this case it would be forbidden according to all, being that the joy of Purim and a wedding is Simcha related, as opposed to a mere skit. [Shevet Hakehasi ibid]
 As the implication from the Poskim is that whenever the dressing is done for jest and not for promiscuity, it is permitted if one’s gender remains recognizable, even if the joy is not for the sake of a Mitzvah.
 Ohel Yaakov p. 287 in name of Harav Gerelitz that it is forbidden for girls in a play to wear a hat or Tzitzis; Orchos Rabbeinu 1/226
 Igros Kodesh 10/238, printed in Shulchan Menachem 5/56