Is Deuteronomy 22:5 applicable today?
The basic principle here is that each of the two sexes is to appreciate and honor the dignity of its own sex rather than to adopt the appearance or role of the opposite sex. If a man is thankful to God that he was created a male and the woman that she was a female, then they should be happy to dress the part of a man or a woman, as the case may be, rather than imitating the costume of another. The specific range of styles worn by each sex tends to differ somewhat from one decade to another, and so it is impractical to lay down any hard and fast rule beyond the simple principle enunciated above.