Deuteronomy 22:5 - Clarke's commentary and critical notes on the Bible

The woman shall not wear that which pertaineth unto a man, neither shall a man put on a woman's garment: for all that do so are abomination unto the LORD thy God. 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.