Deuteronomy 22:5 meaning

Moses then told Israel that a woman shall not wear man's clothing (v. 5). Male and female were to retain their distinct identities. Interestingly, the Hebrew word used for man (Heb. "geber," related to the word "gibbôr," "mighty man") is a term which refers to a male who is at the height of his strength and abilities. The word clothing (Heb. "kelî," "garment", "ornament") can refer to any article normally worn or carried by men such as adornments and weapons. But since the word occurs in parallel with woman's clothing, it is probably used here simply as man's garments.

Just as a woman was not allowed to wear man's clothing, a man could not put on a woman's clothing. Cross-dressing would have at least two negative effects. First, it would violate the natural order of things that the Suzerain (Ruler) God had established. For, although God created male and female equal, He created them with distinctive natural gender (Genesis 1:27, 2:21-24). Thus, to cross-dress would be to confuse genders and act contrary to God's design for human beings. Humanity was created as God's image by being male and female (Genesis 1:27). An example of this is that God created the woman as a "helper." The word for "helper" (Heb. "'ēzer") is most often applied to describe God in the Old Testament (as in Exodus 18:4, Deuteronomy 33:7, 26, 29, Psalm 33:20)

Second, cross-dressing was known to be practiced in paganism to gain the favor of the gods/goddesses or to invoke them to send a message. Thus, it would reflect the religious practices of the pagan nations surrounding Israel, thus suggesting an association with idolatry (Deuteronomy 7:1-5, 25, Leviticus 18:12).

These reasons might explain why Moses told Israel that whoever does these things is an abomination to the Lord your God. The term abomination (Heb. "tō'ēbâ") refers to that which is repugnant or abhorrent in the eyes of the LORD. It can refer to defective sacrifices (Deuteronomy 17:1), the practice of magic and divination (Deuteronomy 18:12), or idolatrous practices (2 Kings 16:3). It also includes sexual perversion, as in Leviticus 18:22-26. The Canaanite nations practiced all these things. The Suzerain (Ruler) God consistently commanded His chosen people to refrain from such perverse practices in order to serve Him as loyal vassals and be set apart as a "kingdom of priests" and a "holy nation" to Him (Exodus 19:5-6). The Canaanite culture was a culture of exploitation (as evidenced in Leviticus 18). Israel was to be a nation of neighbor loving neighbor.

A possible reason this command is housed within the sixth commandment relating to sanctity of life is that sexual confusion is a path to losing one's self.