Humans, by their very nature, relate badly to any 'otherness'. There are innumerable examples - obesity, a hunchback, strong glasses, crooked legs, etc. - that immediately become a reason for mockery, rejection or unpleasant jokes.
Some people do not need any justification for their meanness, while others do - and claim that they condemn this "otherness" because God tells them to or because it is required by "moral norms", without which society would collapse.
I am a Catholic, and I regret to say that many people in church circles mistreat people with gender identity disorders, and people with gynecomastia may be taken as such by the uninformed.
In fact, however, this is just a manifestation of the weakness of church people and has nothing to do with the gospel.
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The replies to this thread are wonderful, insightful, opinionated and informative. Thanks everyone. The explanation about clothing worn by the Israelite people during the wandering years, the years when the Pentateuch laws were being written is probably as close to accurate as we can hope to have. The difference between men's and women's clothing was most likely similar.
A very popular evangelical preacher took the time to explain the importance of the scripture about a man dressing in women's clothing. He enlightened the audience to the fact that the clothing of the period was similar. That the scripture is intended to teach that the individual committing the act of dressing alternatively is doing such as a mode of deception to avoid responsibility. God sees that deception and will condemn the individual.
I believe that if bras were sold in both men's and women's clothing departments, and always had been, we, today, wouldn't be having these discussions.
I have been a bicycle commuter all my life. When my moobs started hanging down in a most unattractive way I purchased a sport bra. When temperatures rose I would remove the shirt and wear the bra only, like so many females do. I got odd stares and occasional chuckles. But I didn't care. Those people were just showing their ignorance. I could just imagine the response if I did not wear a bra for modesty reasons let alone support reasons.
So in regards to this, "dress" was the act of wearing specific articles of clothing. In some cases this included the veil (wholly female) vs. a face scarf men would wear similar to the modern "shemaug" that multiple foreign troops use in places such as Afghanistan similar to the Arabic keffiyeh, as well as colored articles that were gender specific, along with jewelry such as the rabiyd.
Back to the veil; during weddings it was a symbol of before and after a wedding and other traditions. men wore head dresses to keep the sun off of them, but women's head dresses had a specific form, identifying them as such. Those veils were also a symbol of marital status, and other aspects of life.
Typically, such veils in those times also used a crown like (or tiara if you wish) band that kept the veil in place. Scholars are not wholly confident on this, but that band is found in various forms all through the middle east (Asia for you blokes in the UK) including Mesopotamia, Egypt, Syria, the whole of the Levant and such.. Similar veils are found in East Asian areas including China, Mongolia, India and such.
The act of wearing such by men was considered an abomination before God because it mocked his creation first, and switched the established gender roles as spelled out in the Talmud and Torah. (Like saying that one either reads War and Peace or one speaks it...) But more so that it was the intentional portrayal of one as something they physically were not. Male breasts at that time was looked upon as a normal aspect un-condemned similar to passing gas.. it simply was.
Regardless, the gender specific clothing even during the middle ages had many similarities, as well as during the Roman, Greek and Egyptian era.
Where the concern is today is not so much that one wears opposite gender clothing, but that many Christians see the agenda that has been behind the movement is said to be out to destroy Christianity as a whole. This is what is seen by those part of Christianity, and see that gender aspect as a part of a larger beast.
There is no question in my mind that many Christians I know simply do not care, and there are many that do. Its more than ignorance, its interpretation. Because if such gender specific aspects are so absolute, then where is the cry against Indiana Jones wearing a fedora or as previously noted, the wrist watch?
To get hung up on stereotyping is folly. I have met alot of "Christian men" who struggle with similar aspects and rectifying what a preacher tells them over what is a natural aspect of their lives in other ways.