Clothing styles vary considerably by time and place. Still, I believe the Bible gives clear direction about cross-dressing. Men and women by nature groom and dress differently. The Bible mentions this at 1Corinthians 11:14,15; "Does not nature itself teach you that if a man has long hair, it is a dishonor to him; but if a woman has long hair, it is a glory to her? " Deuteronomy 22:5 states clearly God's view of cross-dressing, a view that both Jesus and his true followers share: No garb of an able-bodied man should be put upon a woman, neither should an able-bodied man wear the mantle of a woman; for anybody doing these things is something detestable to Jehovah your God." It is unthinkable that Jesus, who always did what was pleasing to God, would somehow accept what his Father said is detestable.(John 8:29) So I believe that even though Christians are not under the Law of Moses, the principles found in that Law still rightly guide their thinking and conduct.