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Deuteronomy 22:5

A woman shall not be clothed with man's apparel, neither shall a man use woman's apparel: for he that doeth these things is abominable before God.

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The verse in its languages

Vulgate (Clementine)
Non induetur mulier veste virili, nec vir utetur veste feminea : abominabilis enim apud Deum est qui facit hæc.
Septuagint (Swete)
Οὐκ ἔσται σκεύη ἀνδρὸς ἐπὶ γυναικί, οὐδὲ μὴ ἐνδύσηται ἀνὴρ στολὴν γυναικίαν· ὅτι βδέλυγμα Κυρίῳ τῷ θεῷ σού ἐστιν πᾶς ποιῶν ταῦτα.
Hebrew (WLC)
לֹא יִהְיֶ֤ה כְלִי גֶ֨בֶר֙ עַל אִשָּׁ֔ה וְלֹא יִלְבַּ֥שׁ גֶּ֖בֶר שִׂמְלַ֣ת אִשָּׁ֑ה כִּ֧י תוֹעֲבַ֛ת יְהוָ֥ה אֱלֹהֶ֖יךָ כָּל עֹ֥שֵׂה אֵֽלֶּה

Haydock's commentary

God. Some take this literally, as the contrary practice is contrary to decency, and might be attended with very pernicious consequences. All know what noise was occasioned by the action of Clodius, who put on women's apparel, that he might be present with the Roman ladies at the feast of the good goddess. Yet others think that Moses here forbids some superstitious practice. St. Ambrose (ep. 69,) remarks, that in some of the mysteries of the idols, it was requisite for those present to change clothes in this manner, sacrum putatur. Lucian testifies, that men put on women's clothes at the feasts of Bacchus. They did the like in those of Venus, while the women took men's clothes in the festivals of Mars. (Jul. Hirmic. c. 4.) (Maimonides)

In the East, people honoured the moon, to which they attributed both sexes, and Venus in like manner. Josephus ([Antiquities,?] iv. 8,) believes that women are here prohibited to engage in warfare. Hebrew, "the vessels (armour) of man shall not be upon a woman." Semiramis gained a great name by her martial exploits, and commanded all her subjects to dress like herself. (Justin., i)

The Amazons were likewise very famous in war, and it is said that half the army of Bacchus was composed of women. Alb. Gentil maintains that Moses here condemns an abominable crime, which he did not wish to mention, at which the Book of Wisdom hints, (chap. xiv. 26,) and which St. Paul condemns more explicitly, Romans i. 26. Moses had already denounced death against the perpetrators of it; and surely the manner in which he now speaks, seems to forbid something more than simply putting on the garments of the other sex, for he, &c. (Calmet)

Read on

Yet that disorderly conduct deserved to be reprobated in strong terms, (Haydock) when it was not excused by some necessity or proper motive, such as actuated some holy virgins, St. Theodora, &c. (Tirinus)

From Haydock's Catholic Bible Commentary, 1859, in the transcription made by Todd Easton and kept online by John Paul Wohlschied at johnblood.gitlab.io/haydock.

The Fathers on this verse

Clement of Alexandria The Stromata, or Miscellanies, Chapter XVIII. The Mosaic Law the Fountain of All Ethics, and the Source from Which the Greeks Drew Theirs

What reason is there in the law’s prohibiting a man from “wearing woman’s clothing “? Is it not that it would have us to be manly, and not to be effeminate neither in person and actions, nor in thought and word? For it would have the man, that devotes himself to the truth, to be masculine both in acts of endurance and patience, in life, conduct, word, and discipline by night and by day; even if the necessity were to occur, of witnessing by the shedding of his blood. …

St John Chrysostom Homilies on First Corinthians, Homily XXVI

For if exchange of garments be not lawful, so that neither she should be clad with a cloak, nor he with a mantle or a veil: (“for the woman,” saith He, “shall not wear that which pertaineth to a man, neither shall a man put on a woman’s garments:”) much more is it unseemly for these ( Deut. xxii. 5 .) things to be interchanged. For the former indeed were ordained by men, even although God afterwards ratified them: but this by nature, I mean the being covered or uncovered. But when I say Nature, I mean God. For He it is Who created Nature. When therefore thou overturnest these boundaries, see how great injuries ensue.

The Ecumenical Councils The Canons of the Councils of Ancyra, Gangra, Neocæsarea, Antioch and Laodicea, which Canons were Accepted and Received by the Ecumenical Synods, Canon XIII

The synodal letter in its sixth article also speaks of this. Exchange of dress, or the adoption by one sex of the dress of the other, was forbidden in the Pentateuch ( Deut. xxii. 5 ), and was therefore most strictly interdicted by the whole ancient Church. Such change of attire was formerly adopted mainly for theatrical purposes, or from effeminacy, wantonness, the furtherance of unchastity, or the like. The Eustathians, from quite opposite and hyper-ascetical reasons, had recommended women to assume male, that is probably monk’s attire, in order to show that for them, as the holy ones, there was no longer any distinction of sex; but the Church, also from ascetical reasons, forbade this change of attire, especially when joined to superstition and puritanical pride.