“There is not to be.” This verse has been mishandled when it comes to application in our modern culture. It has sometimes been said to refer to “pants” and “dresses,” which is not the case. In the biblical culture, both men and women wore robes, although the length and colors were different—even though some of those differences would be hard for us today to distinguish at first glance. Beyond that, the men wore “things,” such as weapons, that a woman was not to wear, and the women wore “clothing” that the men were not to wear—there was a difference between the clothing, etc., that was worn by the different sexes.
The point of the verse is that God created the two sexes, and the difference between them was to be understood and respected, and was also to be reflected in the way people dressed. C. F. Keil writes about “the divine distinction of the sexes, which was kept sacred in civil life by the clothing peculiar to each sex…The immediate design of this prohibition was not to prevent licentiousness, or to oppose idolatrous practices…but to maintain the sanctity of that distinction of the sexes which was established by the creation of man and woman, and in relation to which Israel was not to sin” (Keil and Delitzsch Commentary on the Old Testament).
Our modern culture does not have strict norms on style of dress like the Israelites had, and men and women wear much of the same clothing. Nevertheless, Deuteronomy 22:5 shows us that God wants us to know and honor the distinction between men and women, and to reflect that honor of His creation in the way we dress. There are clearly ways to dress that are more male or more female, and to purposely dress in such a way as to obscure the distinction in the sexes is, as the verse says, “an abomination to God.”
“a man’s things.” The first half of the verse, about “man’s things,” is more than just clothing, but anything that in that culture would specifically pertain to a man, such as a weapon. In contrast, the second phrase is specifically about woman’s clothing.