Cross-dressing by a skit or play 

Cross-dressing out of jest and fun/Purim/Chasana:^[1]
It is accustomed on Purim [and by Chasunas[2]] to allow males to wear the clothing of females and vice versa.^[3] [However many Poskim^[4] challenge this custom[5] and thus practically one is not to do so. Some write it is to be avoided even by children.^[6] If it is recognizable that the person is a man or woman, and he or she merely wears a single clothing of the opposite gender, there is room to be lenient.^[7] The Rebbe in one letter expressed contempt for children who cross-dress for playful purposes.[8]]

May men/women/children cross-dress for the sake of a skit or play?
No.^[9] 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.^[10] Many however are stringent in all cases[11], and the Rebbe expressed contempt for children who cross-dress for school plays and the like.[12]

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[1] Rama 696/8; Mahriy Mintz 16; Hisorerus Teshuvah 500

[2] Custom mentioned [and negated] in Yireim 96, brought in Taz Yoreh Deah 182/4; Shach 182/7

[3] The reason: This is not forbidden due to the cross-dressing prohibition as the intent is for mere joy [as opposed to promiscuity]. [Rama ibid]

Other opinions in Rama: According to some opinions, there remains a prohibition [for a man to wear women’s clothing, or vice versa, even in such a case]. [Mahariy Brin, brought in Rama ibid and Darkei Moshe 696 regaridng Rabbinical Kilayim and Rama in Darkei Moshe explains that certainly this applies to Lo Silbash] Practically the custom is like the lenient opinion. [Rama ibid]

[4] Opinion [Mahariy Brin] brought in Rama ibid and Darkei Moshe 696; Bach brought in Taz Yoreh Deah 182/4 [Taz concludes “One who is stringent is blessed”]; Shach 182/7; Yireim 96 negates the custom; Teshuvas Harambam; Shalah; Kneses Hagedola; M”B 696/30; Kisei Eliyahu 696/3; Birkeiy Yosef 696/13 and Yoreh Deah 182/3; Beis Oved 696/10; Kaf Hachaim 696/57; Aruch Hashulchan 696/12

[5] The reason: As the allowance to wear clothing of the opposite gender for mere playfulness is only in a case that one does not appear like the opposite gender, being that he/she remains wearing clothing of also his/her gender. [See Shach ibid and Atzei Levona 182]

[6] Piskeiy Teshuvos 696/14; Nitei Gavriel 75/7

[7] P”M 696 M”Z 4; M”B 696/30 in name of P”M; Implication of Shach 182/7 as explained in Atzei Levona

[8] Igros Kodesh 10/238, printed in Shulchan Menachem 5/56

[9] 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]

[10] 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.

[11] 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

[12] Igros Kodesh 10/238, printed in Shulchan Menachem 5/56