The Literal Commandment

A woman shall not wear man's clothing, nor shall a man put on a woman's clothing; for whoever does these things is an abomination to the LORD your God. (Deuteronomy 22:5)

 

The literal commandment is that men should not put on (i.e., wear) women's clothing.

It is one of only about two dozen or so things that G-d calls an abomination.

 

Messiah Says

Messiah implicitly affirmed this commandment when He spoke about the Law:

"Do not think that I came to abolish the Law or the Prophets; I did not come to abolish but to fulfill. For truly I say to you, until heaven and earth pass away, not the smallest letter or stroke shall pass from the Law until all is accomplished. Whoever then annuls one of the least of these commandments, and teaches others to do the same, shall be called least in the kingdom of heaven; but whoever keeps and teaches them, he shall be called great in the kingdom of heaven. (Matthew 5:17-19)

 

Pictures of Messiah

This commandment indicates that we should not depart from the way G-d has ordered His creation. Birds do not put on scales and attempt to be fish. Snakes do not put on fur and attempt to be bears. This commandment pictures Messiah's complete obedience to G-d's order for creation.

Even in His greatest grief (Matthew 26:38), He sought the Father's will:

And He went a little beyond them, and fell on His face and prayed, saying, "My Father, if it is possible, let this cup pass from Me; yet not as I will, but as You will." (Matthew 26:39)

 

Messiah knew His role in Creation and stood firm even in the face of execution to remain in that role and perform His work.

 

How Messiah Fulfilled

We know that Messiah was without sin (Hebrews 4:15) so we know Messiah fulfilled this commandment and did not wear women's clothing.

 

Traditional Observance

This commandment is observed in various ways by different sects.

Some sects simply require that men not wear women's clothes (hence different button and zipper patterns between women's and men's clothing) focusing on the intended audience of the clothing when it was made.

Some sects require that women wear dresses and men wear pants focusing on the form of the clothing and with which sex it is traditionally associated.

Other groups forbid men from adorning or "embellishing" themselves in the manner of women: coiffed hair, earrings, makeup, coloring hair, etc.

 

Other Notes

We are able to fulfill this commandment today, and men should not wear women's clothing.

 

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