The King James Version with Strong's Numbers:
Deu 22:5 The woman H802 shall not H3808 wear H1961 that which pertaineth H3627 unto a man, H1397 neither H3808 shall a man H1397 put on H3847 a woman's H802 garment: H8071 for H3588 all H3605 that do H6213 so H428 are abomination H8441 unto the LORD H3068 thy God. H430
H1397 ("man") is the operative term. Which connotation should be applied? H1397 ("man") is "geber" in transliterated Hebrew. According to Strong's, there are 65 occurrences of geber in the JKV. According to the King James Concordance, there are 70 occurrences. The connotation intended for each occurrence is debatable. Scholars disagree.
Adam Clarke's Commentary on the Bible states:
The woman shall not wear that which pertaineth unto a man - כלי גבר keli geber, the instruments or arms of a man. As the word גבר geber is here used, which properly signifies a strong man or man of war, it is very probable that armor is here intended.... It certainly cannot mean a simple change in dress, whereby the men might pass for women, and vice versa. This would have been impossible in those countries where the dress of the sexes had but little to distinguish it, and where every man wore a long beard.
Clarke highlights the debated issue. However, Deuteronomy was for the Israelites. They had a dress code of sorts, sorting out males and females.
It seems to me that Deu 22:5 was aimed at the Israelites to keep the men (sex) warriors and the women domestic. It seems to be extreme, militant nationalism for the sake of empire, which strikes me as anti-Christ: Old Testament versus New Testament.
So, does Deu 22:5 apply to Christians? If one considers circumcision, it certainly can't be ruled out that Deu 22:5 does not apply. The issue was never addressed the way circumcision was. If it had been, the same arguments today and the same logic then would probably have prevailed. Clarke's point about gentile nations with no truly distinct male/female dress codes would very likely have come up. I should think that the Christian council would have handled dress (men in what were unisex skirts) the way it handled circumcision. It officially/formally allowed the uncircumcised to become members of the church and did not require them to be circumcised (did not require them to follow the Jewish religious law regarding circumcision).
Gentile men in skirts were converting to Christianity in droves, and the fact that they were in skirts never came up as an obstacle or matter for debate. Jewish men were wearing tunics (open bottom, not pants). Jesus wore a tunic. Paul wore a tunic. Paul's concern was with effeminacy, which apparently wasn't determined by him to be a matter of whether one wore a skirt.
Regardless, we need to define the term effeminacy as he originally intended and more importantly determine whether every word that came out of the mouth of Paul jibed in letter and spirit with the Gospel message of Jesus. As far as I'm concerned, Paul made huge mistakes in his understanding of the message of Jesus. The most significant is where Paul tells us to obey the powers that be. Jesus didn't do that, and he told us to obey the higher law even if it meant being martyred for doing so.
Effeminacy clearly is not wearing a skirt, per se. Skirts are worn by plenty of males in the world who generally are not considered effeminate. However, is anti-male effeminacy (in the modern sense) the actual position of Jesus?
A male certainly didn't have to be a Deu 22:5 warrior in order to be accepted by Jesus. In fact, while Jesus would accept such a person, he would admonish that one not to engage in violence. How many people are confused today into thinking that the anti-violent male is necessarily feminine?
However, just how much may a male be in touch with his feminine side (in the modern sense) before crossing a forbidden line? I don't have the Christian answer to that (yet). I do accept transsexuals, as I accept intersex people.
Regardless, I have no problem with men in skirts or other open-bottom clothes whatsoever. Open-bottom clothes for men help raise their testosterone. Therefore, wearing open-bottom clothes cannot be inherently effeminate.