What does the Bible say about cross-dressing / transvestism? Is transvestitism a sin?

Verse 5 forbids a woman to wear man's clothing or a man to wear women's clothing, for it is an abomination to thus try to pass as a member of the opposite sex. If God has created one as a man, it is an insult to God for him to outwardly take the place of a woman, and similarly for a woman to take a man's place. Let us rather be thankful for what God has made us and seek to bear faithfully the responsibilities of that place as well as to enjoy the blessings of it.

Laws on the second table are now more fully expounded by Moses. The love to the neighbor is to be expressed by guarding and preserving that which is his property. The strayed and fallen animal belonging to another had to be helped. To leave them in that condition would have been a violation of the law "love thy neighbor as thyself" as well as an act of inhumanity. Another interesting law is the one which forbids woman to wear man's garments (verse 5). "The immediate design of this prohibition was not to prevent licentiousness, or to oppose idolatrous practices; but to maintain the sanctity of that distinction of the sexes, which was established by the creation of man and woman, and in relation to which Israel was not to sin. Every violation or wiping out of this distinction--such as even the emancipation of women--was unnatural, and therefore, an abomination in the sight of God." Yet to-day we find a universal movement in the world for the complete emancipation of women, which ignores and even defies the place which the Creator and the Redeemer has given to woman.

The disguise as to sex would plainly serve all kinds of fraudful and dishonest purpose, whilst it falsified the stamp which God has put upon nature, and mutilated, so to speak, the coin of His realm. The taking the mother-bird, held by her affection to her young, was shameful advantage used of natural instincts, and a violation of honor to parents in this reproduction of motherly love in the lower creatures. The repetition of the promise here is very striking. It shows how sensitive will be the really obedient heart, and how God has in nature encompassed us with remembrances as well as tests of our condition. The law as to the battlements for the flat roofs of houses is simple enough as a rebuke of that thoughtlessness which is really hardness of heart. The three laws which follow as much resemble one another as they differ from what goes before. As prohibitions of mixture they come naturally enough under the first head here. The interpretation of the unequal yoke" is plainly given in 2 Cor. 6:14. Christ's yoke cannot be borne by the unclean — the unbeliever, — and for the believer there is no other. The garment of woolen and linen speaks similarly of mixed habits; while the sowing seed represents the necessity of keeping the truth unmixed. Failure in all these points involves a real robbery, not only of God, but of one's neighbor: we owe both to Christians and the men of the world the maintenance of our Christian simplicity and singleness of life and testimony. The last thing here, the tassels upon the garment, which we have had in Num. 15:38, reminds us that this is to be true natural development — the development of the new nature, not artificial, for the word speaks primarily of flower-buds. How beautifully again does the spiritual meaning declare the perfection of the Word of God!

Thus we see, even from the natural point of view, God expressing His mind in most unmistakeable language, and branding with the mark of shame every woman who, even if only in her garment, disowns the place in which the Lord has put her. I can but refer to what has been said already on this subject in chapter two when speaking on the principle of divine order.

Deuteronomy 22 appears to contain ordinances to guard the people from want of benevolence and mercy, and of that which would offend the sensibilities of nature, either with regard to tenderness or purity. So also all mixture was forbidden in ploughing or sowing. We find the same with regard to women: they were protected against the dishonour done to them by a brutish, inconsiderate husband; whilst impurity was punished with death.

To correct this disorder the Apostle takes a way often adopted in Scripture to settle questions. In order to learn the principles involved in any question or difficulty, we are taken back to the first occasion of the principles being set forth. Here, a question having arisen as to the relative position of men and women, we are taken back to the order first established in creation. It is true that in Christ — in the new creation — “there is neither bond nor free, there is neither male nor female”. In the old creation, as in the assembly, these distinctions still exist. Christianity, however great the common privileges it confers, does not set aside the order of creation, and, while in these mortal bodies in a scene where these differences exist, the Christian is responsible to observe this order.

In I Corinthians 11:14, 15, the apostle refers to nature as a further evidence of the distinction between man and woman and of her proper place of subjection. "Does not even nature itself teach you, that man, if he have long hair, it is a dishonor to him? But woman, if she have long hair, (it is) glory to her; for the long hair is given (to her) in lieu of a veil" (New Trans.). God has given long hair to woman and short hair to man as a distinguishing mark between them. It is natural for woman to have long hair and for man to have short hair.

In Deuteronomy 22 we have a group of different institutions as to questions of righteousness, care, love, tenderness — the smallest matters as well as the greatest — but they are so numerous, in themselves purposely the minutest as well as the most momentous, that to dwell on them one by one would occupy much too long for the present design. All can understand however how the great object here is that God would form the heart of His people in this relationship and measure according to His own affections. God would give them not bare righteous but holy thoughts, and not this only, but mingled with tenderness when called for. This will be found true if the contents of the chapter be duly weighed.

We can say, Isaiah 61, verse 10, “for He hath clothed me with the garments of salvation, He hath covered me with the robe of righteousness, as a bridegroom decketh himself with ornaments, and as a bride adorneth herself with her jewels.” Clothing, garments, speak not only of the moral state of the person but also of his testimony. The first thing you see in a person is his garment.