Deuteronomy 22:5

To befriend a lawful escape or concealment it may be done, but whether for sport or in the acting of plays is justly questionable. Some think it refers to the idolatrous custom of the Gentiles: in the worship of Venus, women appeared in armour, and men in women's clothes; this, as other such superstitious usages, is here said to be an abomination to the Lord.

The woman shall not wear that which pertaineth unto a man,....

That which pertaineth unto a man - i. e. not only his dress but all that especially pertains distinctively to his sex; arms, domestic and other utensils, etc. The distinction between the sexes is natural and divinely established, and cannot be neglected without indecorum and consequent danger to purity (compare 1Co 11:3-15).

The woman shall not wear that which pertaineth unto a man, neither shall a man put on a woman's garment--Though disguises were assumed at certain times in heathen temples, it is probable that a reference was made to unbecoming levities practised in common life.

The woman shall not wear that which pertaineth unto a man - כלי גבר keli geber, the instruments or arms of a man. As the word גבר geber is here used, which properly signifies a strong man or man of war, it is very probable that armor is here intended; especially as we know that in the worship of Venus, to which that of Astarte or Ashtaroth among the Canaanites bore a striking resemblance, the women were accustomed to appear in armor before her. It certainly cannot mean a simple change in dress, whereby the men might pass for women, and vice versa. This would have been impossible in those countries where the dress of the sexes had but little to distinguish it, and where every man wore a long beard. It is, however, a very good general precept understood literally, and applies particularly to those countries where the dress alone distinguishes between the male and the female. The close-shaved gentleman may at any time appear like a woman in the female dress, and the woman appear as a man in the male’s attire. Were this to be tolerated in society, it would produce the greatest confusion. Clodius, who dressed himself like a woman that he might mingle with the Roman ladies in the feast of the Bona Dea, was universally execrated.