Deuteronomy 22:5

Pants are considered to be exclusively male clothing even by some contemporary Christians, yet there is nothing "male" or "female" about mere cloth.  Biological anatomy and physiology dictate one's gender; psychological and cultural variables are merely individual or social factors, and clothing falls into the latter category.  There is no logical connection between pants and men or dresses and women, for example.  There is only a general expectation that certain clothing will be worn by either men or women in specific cultures.

Women have worn pants for many years in Western culture, and men have historically worn clothing that resemble dresses far more than they resemble modern male clothing (in the West, at least).  In neither case has a person committed an act that is inherently wrong by Biblical standards.  No particular style of clothing is sinful, no matter how foreign, "strange," sensual, or revealing it is.  Of course, none of those qualities (the objective and subjective ones alike) make a certain type of clothing, like pants, "male" or "female."

However, Deuteronomy 22:5 does prohibit the wearing of clothing belonging to the opposite gender.  Given that it is a logical fact that clothing styles are not tied to gender and are not Biblically prescribed (meaning they are not obligatory), it is important to clarify why the command of Deuteronomy 22:5 does not actually conflict with the logical disconnect between clothing and gender.  Instead of prescribing a particular set of clothing for men and another for women, it is only a condemnation of wearing clothing that a given culture has arbitrarily associated with either gender.

Cultural expectations usually change over time, and consensus and tradition never make a particular action morally obligatory or immoral.  All the same, without cultural clothing norms for each gender, the obligation in Deuteronomy 22:5 could not be fulfilled, though the obligation itself is not rooted in culture.  Clothing that is culturally regarded as androgynous or "unisex" is exempt from this prescription because it is not socially associated with either gender, but there are still certain types of clothing associated with men and women in the Western world that the verse would confine to one gender.

If 51% of a society decided to suddenly shift the public expectation for women to wear dresses and associate them with men, for example, no one could say that the majority of the culture affirms the former standards.  If a single person dresses in clothing that is explicitly, almost exclusively associated with one gender, they could not claim to have changed the societal norm.  Thus, the latter individual would violate the command in Deuteronomy 22:5, but the former individuals would not.

It is in this way that Deuteronomy 22:5 still applies in specific cases despite clothing and gender being things that have no non-cultural connection whatsoever--and despite moral obligations having nothing to do with personal or cultural preferences.  The verse does not say that men or women must wear certain clothing styles, like pants or dresses respectively, that unisex clothing is sinful, or that people have to wear clothing in the first place (nudity is nonsinful, as Deuteronomy 4:2 and other verses confirm).  It merely condemns wearing clothing that is generally associated with the opposite gender in a given cultural context.