Does the Bible say anything about cross-dressing / transvestism? Is it sinful to cross-dress? Is it wrong to be a transvestite?

from the old testament

• God made humanity in His image, both men and women (Genesis 1:27). God uniquely made us male and female, and as we live according to the biological sex in which He made us, we display His order, goodness, and purpose, rather than redefining it by our own desires.
• Deuteronomy 22:5 says, "A woman shall not wear a man's garment, nor shall a man put on a woman's cloak, for whoever does these things is an abomination to the LORD your God." According to the Law of Moses, cross-dressing was clearly prohibited. Scholars on Deuteronomy note that cross-dressing would have likely been associated with homosexuality or would have been considered associated with the practices of other religious groups.

from the new testament

• The New Testament does not specifically address the clothing of men and women other than a call to modesty (1 Timothy 2:9–10).
• The closest parallel in the New Testament to Deuteronomy 22:5 is related to the length of a man's or woman's hair in 1 Corinthians 11:3–15. This passage focuses on understanding and living according to the gender by which God created each person. There was to be no confusion among Christians whether the person was a man or woman. This implies that cross-dressing is wrong. Presenting oneself as a different gender goes against scriptural principles.
• While cross-dressing is inappropriate, it is also clear that Christians are called to show God's love to all, regardless of how they present themselves. In the case of a person who cross-dresses or is a transvestite, the goal is to "honor Christ the Lord as holy, always being prepared to make a defense to anyone who asks you for a reason for the hope that is in you; yet do it with gentleness and respect, having a good conscience, so that, when you are slandered, those who revile your good behavior in Christ may be put to shame" (1 Peter 3:15–16).
• Though we should treat others with respect, we should never participate in or encourage their sin. For example, we should never affirm a gender for someone that doesn’t represent reality (e.g., calling a man “she” or a woman “he”). This would be lying, which is condemned throughout the Bible, including the New Testament (Ephesians 4:25; Colossians 3:9).

implications for today

Some conservative Christians have taken Deuteronomy 22:5 to mean a woman cannot wear pants or slacks. This would be a misapplication of this and other passages in the New Testament regarding modesty. The clear focus is God's emphasis that men and women should not seek to appear as the opposite gender and that to do so is considered shameful. In Western culture, pants are regularly worn by both genders. Further, Deuteronomy 22:5 is part of the Mosaic Law fulfilled in Christ , so it does not require the same direct application, though the principles behind it still apply.

Christians are called to dress in appropriate ways. Women are commanded in the New Testament to "adorn themselves in respectable apparel, with modesty and self-control, not with braided hair and gold or pearls or costly attire" (1 Timothy 2:9). Men were not to show favoritism to a man who came to a church gathering in rich clothing (James 2:1–4). In these examples, it was not the braids or specific articles of clothing that were the problem, but the extravagance in comparison with others in the church. Instead, believers are to dress with modesty appropriate to their surrounding culture. The issue is one of the heart. The way we dress should honor God and His design for us.