Cross-dressing, considered by some of little consequence today, was strictly forbidden in Israel because it obliterated the lines of distinction inherent in God’s creation of man and woman.
APOLOGETICS STUDY BIBLE
The term often associated with a cross-dresser is transvestite—that is, someone who dresses opposite to his or her assigned gender. Interestingly enough, this doesn’t mean that a male dressing up as a woman is a homosexual. It can, but as odd as this may sound it doesn’t necessitate it. Gender issues can be very complex, and cross-dressing just adds another shade to the “fifty shades of gender” culture that we inhabit. Some people cross-dress because they don’t feel their gender identity matches the gender they were assigned at birth. Others cross-dress simply as a fashion statement. They like the clothing of the opposite sex better so a guy may sport a dress or wear some high heels all in the name of “I like it.”
As much as one may like the attire of the opposite sex, cross-dressing is prohibited in Scripture. The Bible says, “A woman shall not wear a man’s garment, nor shall a man put on a woman’s cloak, for whoever does these things is an abomination to the LORD your God” (Deuteronomy 22:5). The obvious principle that surfaces for us from this verse is that men should embrace their manhood and women should embrace their womanhood. Cross-dressing is an abomination because it is an outright rejection of God’s design for us.
That’s the real issue.
This verse comes from the Old Testament—from the law—but the principle hasn’t rusted out with the ticking of time. In such cases, it’s important to get at the principle tucked beneath the commandment. In this case, the overarching principle is that the Scriptures oppose cross-dressing because it portrays a rejection of one’s divinely assigned gender (see Genesis 1:27). We are to embrace our gender. Not seek to erase it.
Thought to Ponder
Gender isn’t a preference issue; it’s a design issue.
Memory Verse
A woman shall not wear a man’s garment, nor shall a man put on a woman’s cloak, for whoever does these things is an abomination to the LORD your God (Deuteronomy 22:5).
One-Minute Apologist Video: Bobby Conway, “Is Cross-Dressing Permissible?”
Life Less Ordinary 
I agree. I would add, though, that intention is important when applying this commandment. Men who wear women’s clothing to entertain and amuse others are not de facto breaking this commandment. As you describe, those who seek to blur their gender are in violation of the commandment. J.
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I still cannot understand why a man would want to wear high heels. I’m a woman and I don’t like wearing them. Give me a sweet pair of boots any day!
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I agree
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Just some questions to consider:
-Would you really not recognize a male as a male when wearing heels?
-Why would you be confused and in which way would that change the interaction?
-Would people from other places and from other times consider our destinct male/female clothing as well-defined?
-Would some define in the opposite way?
-Is the evaluation of clothing depending of our environment?
-Since when is it acceptable for women to wear trousers?
-Which variations would be okay and which would be exceeding?
-Who defines what is male and what female?
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it is a metter of freedome on their requirement, liking and most important whats makes her or him more comfortable. If a male like to wear women dresses, Thats his desire. simply a matter of happiness, and I feel , no one should any objection.
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