Deut. 22:5 - " The woman shall not wear that which pertaineth unto a man, neither shall a man
put on a woman's garment: for all that do so are abomination unto the LORD thy God ."
There's no mention of 'skirts' or 'trousers' in that verse. The substance of that injunction is that
men and women should not confuse their gender appearances; and the motive is to discourage the
lifestyles that may stem from such practices.
Confusion of appearances lead to confusion of gender roles. Such lifestyles may include homosexual tendencies among God's people, which is another abomination (Lev.20:13); or gender roles confused altogether, in the family and society at large.

It is interesting that the dress-sense and fashion of the Old Testament people included the idea
that men and women wore garments that had skirts. Notice the masculine pronouns used in
Psa. 133:2 - "It is like the precious ointment upon the head, that ran down upon beard,even Aaron's beard: that went down to the skirts of his garments " and of Ezekiel: " Thou shalt also
take thereof a few in number, and bind them in thy skirts" (Ezek. 5:3). So men wore garments that had skirts back then, but not in the sense of skirts' (a woman's garment which hangs down from the waist) as we understand them today.
The skirts of Aaron's garment were simply in reference to the outer border of the priestly garments.
Several ancient and contemporary civilizations and cultures had and have clearly defined gender
dress modes. Even today, the Scots are popular for their kilts (knee-length pleated skirt of tartan
wool which is worn by men as part of the
traditional dress of the Scottish Highlands). Other
traditional dresses worn by both gender in some
other cultures include (a) the sarong - skirt made
from a piece of fabric wrapped around the body
and fastened at the waist and worn by men and
women in Malaysia and other Pacific islands; (b)
the toga - loose draped garment worn by citizens
of Ancient Rome; (c) robe - any long loose
garment (including the gown); and other types like
(d) the tunic - usually long upper garment worn
by women, but for the men depicts loose-fitting
garment often without sleeves and often belted:
worn in ancient Greece and Rome.
Some believers assume that Deut. 22:5 is
condemning women wearing trousers and men
wearing skirts. However, that is not what
Scripture indicates. As we have seen, the
substance and motive for that verse is to
discourage any confusion of gender identity and
roles among people professing to belong God.
There are professional vocations that require a
dress code that include the idea of trousers worn
by both men and women, such as civil and
petroleum engineering (the overalls they wear in
field of operation), and some military service
posts. I remember during our NYSC orientation,
some ladies wanted to make an issue out of the
khaki trousers; they wear given the option of
either following the call of orientation service or
quit camp.
Of course, what you wear tells who you are. In
the NT, women are particularly admonished to
"be modest and sensible about their clothes and
to dress properly" as befitting women professing
to be godly. (I Tim. 2:9, 10). Men and women
who profess godliness in their lives don't want to
misrepresent their calling, and that's why we're
admonished in the OT verse above to not mix up
our dress sense to risk confusing our gender
identity and roles, because "from the beginning of
the creation God made them male and
female" (Mark 10:6).

Yes