Men’s and women’s clothing

With all the changes of how people dress throughout history and more recently within the last 50 years of how women dress more like men, what is the view of men dressing like women? Is it OK for women to dress like men as it appears it is socially acceptable in society and when attending church? Is it OK for men to dress like women? Didn't the men and women in biblical times dress similarly? This question is in regard to cross dressing only without being involved in homosexual activities.

In Deuteronomy 22:5 God had instructed Old Testament Israel:  “A woman must not wear men’s clothing, nor a man wear women’s clothing, for the LORD your God detests anyone who does this.”  The People’s Bible Commentary on Deuteronomy provides a good explanation of that command and a response to your question.

“While this law might sound like a blanket prohibition against wearing any clothing ordinarily worn by the opposite sex, some commentators have seen a deeper meaning here.  There was a connection between cross-dressing and some features of Canaanite fertility religion.  Worship directed to Astarte, the twin sister of Baal, sometimes featured men masquerading in women’s clothing and women appearing in men’s clothing.  Homosexuality was also associated with Baal worship.

“The New Testament contains no hard-and-fast regulations for the kind of clothing God wants his people to wear, but it does include general principles for people of all times.  Peter told women, ‘Your beauty should not come from outward adornment.’  Such outward adornment will take various forms and styles in different cultures.  ‘Instead, it should be that of your inner self, the unfading beauty of a gentle and quiet spirit, which is of great worth in God’s sight’ (1 Peter 3:4).  Paul urged women to ‘dress modestly, with decency and propriety’ (1 Timothy 2:9).  Paul told the Corinthians that ‘every man who prays or prophesies with his head covered dishonors his head.  And every woman who prays or prophesies with her head uncovered dishonors her head’ (1 Corinthians 11:4, 5).  The details of the Corinthian custom aren’t entirely clear to us, but God wants the customs among any group of people faithfully to reflect the roles he’s designed for men and women.

“Styles change from one time and place to another; it’s impossible to dictate a specific dress code for all the rest of human history.  God wants men and women to appreciate the dignity of their own sex, instead of assuming the appearance or preferring the role of the opposite sex” (pp. 197-198).

To those thoughts I would add the reminder of what Christian freedom is all about.  In areas of Christian freedom I am mindful of what is in the best interests of others and how my actions might negatively affect them.  While Christian freedom means that I can pursue a course of action, Christian freedom also means I have the right not to do something.