Deuteronomy 22:5 KJV says, The woman shall not wear that which pertaineth [keli]of a man [geber], neither shall a man [geber] put on a woman’s garment [simlah]: for all that do so are abomination unto the LORD thy God.
We have looked at how a geber-man was a mighty man or man of valor. The first definition of keli given in the concordance pertains to general things, such as utensils and vessels, and not things worn. So we are after the second definition which pertains to things a geber-man would wear:
2 utensil, implement, apparatus:
a. implement of hunting and (especially) war, = weapon Genesis 27:3 (J), 1 Samuel 20:40; 1 Samuel 21:9 (גַּם חַרְבִּי וְגַם כֵּלַי), 1 Kings 11:8 2 Chronicles 23:7; 1 Kings 11:11; Isaiah 54:16,17; Jeremiah 22:7; probably also Numbers 35:32, כְּלִי בַּרְזֶל Numbers 35:16, כְּלִי עֵץיָֿד Numbers 35:18 (all P); כְּלֵיחָמָם Genesis 49:5 (poem); כְּלִי מַשְׁחֵתוֺ Ezekiel 9:1, מַמָּצוֺ׳כ Ezekiel 9:2; figurative of God’s weapons כְּלֵימָֿוֶת Psalm 7:14 (“” חִצָּיו); זַעְמוֺ׳כ Isaiah 13:5; Jeremiah 50:25; of entire equipment of warrior, armour or armament offensive and defensive 1 Samuel 17:54 (compare 1 Samuel 17:5 ff.), 1 Samuel 21:6 (twice in verse) (see Dr Sm 139. 293), 1 Samuel 31:9,10 = 1 Chronicles 10:9,10; hence נשֵֹׁא כֵלִים (כֵּלָיוׅ armour#NAME? weapon-bearer Judges 9:54; 1 Samuel 14:1,6,7,12 (twice in verse); 1 Samuel 14:13 (twice in verse); 1 Samuel 14:14,17; 1 Samuel 16:21; 1 Samuel 31:4 (twice in verse); 1 Samuel 31:5,6 = 1 Chronicles 10:4 (twice in verse); 1 Chronicles 10:5,2Samuel 18:15; 2 Samuel 23:37 = 1 Chronicles 11:39; figurative וְכֵלַי כֵּלָיו רָעִים Isaiah 32:7 and a knave, his weapons (i.e. devices, Che ‘machinations’) are evil; more precisely כְּלֵי מִלְחָמָה Judges 18:11,16,17; 1 Samuel 8:12; 2 Samuel 1:27; Deuteronomy 1:41; Jeremiah 21:4; Jeremiah 50:20 (figurative), Ezekiel 32:27; 1 Chronicles 12:34 (van d. H v. 1 Chronicles 12:33); כְּלֵי צְבָא מִלְחָמָה 1 Chronicles 12:38 (van d. H v. 1 Chronicles 12:37); כְּלֵי קְרָב Ecclesiastes 9:18; בֵּית כֵּלָיו 2 Kings 20:13 = Isaiah 39:2 is perhaps armoury; ׳כ Ezekiel 40:42 is sacrificial knife.
Source: Brown-Driver-Briggs Hebrew #3627
The word “wear” is not actually found in the first part of the verse. The Young’s Literal Translation renders it thus:
The habiliments of a man are not on a woman, nor doth a man put on the garment of a woman, for the abomination of Jehovah thy God is any one doing these.
But there is more here to uncover. The most literal translation would be this:
And HE IS NOT a weapon of a valiant-man on a woman, and a valiant-man is not wearing a garment of a woman, for an abomination of Yahweh thy God is the whole of him-who-makes these ones.
“Weapon” [keli] is from a singular noun. It is not in the plural. The NASB translates this word keli as “armor” 24 times and “weapons” 22 times. That is significant. The only meaning that gets rendered more, is “utensils” or “vessels” which are not things worn. But because “wear” is not a part of the first clause, one can surmise what a “utensil of a valiant-man” might be.
“Him who makes” comes from a participle verb עֹ֥שֵׂה to make/do in the masculine singular. It is not in the plural.
The last word “these” is a plural pronoun (#428).
So what does it mean?
In the fully literal translation this sounds much more like a riddle that one has to figure out, does it not?
He is not a weapon of a warrior on a woman.
The warrior is not wearing a garment of a woman.
An abomination is the whole of the one who makes these.
Taken as rule, one can see how obscure and impossible it is to arrive conclusively at anything enforceable. It seems to be talking about cross-dressing…but give no useful information, boundaries, explanations, or lines. How can one transgress the line when there are no lines?