Today: We know it is generally considered wrong if a man dresses up in women clothing trying to look like a woman, and if it is wrong for a woman to dress using men's clothing that does not really fit them in attempt to look more like a man. The heart of this rule I believe is... does a person appear to look like the opposite sex by the type of clothing that they are wearing today? Are they wearing more men's clothing than women's clothing? This is at the heart of the issue here.
Yes, I do believe we have to take culture into consideration here. At one point in time, In our culture, it was considered unacceptable in English speaking countries for women to wear pants. This has appeared to have changed in World War II.
Check out this article here:
A brief history of women’s fight to wear pants
Today: A person does not regard a woman wearing pants as dressing like a man or with them attempting to be more masculine (Even though it meant that way in the past and it could include imprisonment).
Today: Unless one is a Scottish man blowing on some bagpipes, it is generally considered an effeminate thing for a man to wear a woman like skirt.
1 Corinthians 6:9 says, “Know ye not that the unrighteous shall not inherit the kingdom of God? Be not deceived: neither fornicators, nor idolaters, nor adulterers, nor effeminate, nor abusers of themselves with mankind,”
Granted, even Bible clothing was like that of a long dress. For to girt up the loins of truth in Ephesians 6 (in regards to the armor of God) was when a man would wrap up his cloak around his legs in order to fight in battle.
But, if an American were to see this kind of garment today, we would not think they are dressing like a woman. They still look masculine. But if they were to wear clothes in such a way that women wear today that is clearly identified with what women wear today, then that is wrong. Our culture has a lot to do with it. But the overall rule of thumb is common sense. Do they look like the opposite sex by their clothing? Are they wearing actual clothing that comes from the opposite sex that is clearly for the opposite sex only? I am not talking about T-shirts here (Which one cannot tell the difference between a woman sized T-shirt, and a man's sized T-shirt). It's obviously not wrong for a woman to wear a man's sized T-shirt. But if they were to wear men's jeans, and put on a big belt buckle, and tuck in a plaid shirt and wear really large men's boots as a part of their normal every day appearance, then obviously there is a problem. I think most people know when a person is dressing more like a woman vs. a man.
Granted, while we are not under the entire package deal of the Old Covenant Law of Moses given to Israel (For we do not sacrifice animals, circumcise, etc), and while our culture of dress may have been different than the Israelite, Deuteronomy 22:5 is still a moral law and can be applied for us today in our culture. At the heart, this verse is condemning one trying to look like the opposite sex by one's clothing within their culture. So if your Pastor is wearing a lot of pink sweaters, his nails are colored, and you see him in a woman's skirt,.... run for the hills; For he is in error.