"A woman shall not wear man’s clothing, nor shall a man put on a woman’s clothing; for whoever does these things is an abomination to the Lord your God." (Deut. 22:5).
This admonition most probably deals with the mandate to maintain the distinctions between male and female functions and roles. "Cross-dressing" seems to be the issue here. The man is not to be feminine, and the woman is not to be masculine. Neither is to assume the manerisms and role of the other. Also, the created order distinguished between male and female very clearly and adopting the clothes of the opposite sex would blur this line and might even encourage homosexuality.
The same Hebrew word translated detests (to ebah, lit., ”a detestable thing;" kjv, ”an abomination“) is used to describe God’s view of homosexuality (Lev. 18:22; 20:13). Also some evidence exists that transvestism may have been connected with the worship of pagan deities. Since this law was related to the divine order of Creation and since God detests anyone who does this, believers today also ought to heed this command."1
- 1. Walvoord, John F., and Roy B. Zuck, The Bible Knowledge Commentary, Wheaton, IL: Scripture Press Publications, 1985.