The notion as to whether a person is a cross-dresser or not is to a very large extent a socially constructed one, and one only has to consider women wearing jeans and trousers to grasp the point.
There are presently societies such as Scotland where the kilt is frequently worn by men, and in Malaysia and other Pacific islands where both men and women wear sarongs, and in none of these places are the wearers considered cross-dressers or deviants.
The Bible states that women must not dress in men's clothes and in the book of Deuteronomy (22:5) cross dressing is said to be an "abomination", as is homosexuality.
But as the world shrinks, it is likely that people will be more and more accepting of dress codes that are acceptable in other countries, and neither support hose for men with bad circulation, or the wearing of bras for men with gynecomastia presently cause much more than the raising of an eyebrow.