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.

Deuteronomy 22:5

The Church has traditionally held views on transvestism similar to those on homosexuality. In support it has been able to cite Deuteronomy 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 to the Lord thy God.

So it was that one of the main accusations against Joan of Arc, which ensured her death at the stake, was that she insisted on wearing men's clothes.

Joan was convicted and condemned for transvestism by the Catholic Church.
They made point of burning her in orthodox female attire.

Transvestism was also one of the reasons the Church so disapproved of theatre. Having forced women off the stage acting troupes had no choice but for men to play women's parts, and right-thinking Christians found this nearly as bad as seeing real women on stage.

Rational Dress Reformers campaigned for women to be able to wear trousers.. They claimed that corsets and heavy skirts made women prisoners of their own clothes, arguing that traditional clothes were unhygienic. Turning the conservatives' argument around they also argued that traditional clothes were immoral because they changed a woman's shape for fashion. Pro-corset conservatives argued that looking respectable and being properly dressed was a Christian lady's duty, however uncomfortable it might be. When Amelia Bloomer lobbied in her newspaper for a shorter dress over loose "bloomer pants," (worn during exercise) she was widely ridiculed, Practical clothing, like exercise, was too radical. Both were considered dangerous by traditional Christians. Christian doctors advised against them, claiming (falsely) that they would damage womens' fertility. "Bloomers" became a staple of music-halls, and the word is still used with mockery today.

Women dressing as men was considered immodest and immoral, and contrary to the bible. Rules had been enforced by Church Wardens but from the nineteenth century they were enforced by newly formed police forces. Rules were enforced, even in places with a reputation for relative freedom. Municipal records in San Francisco show that one "Marie Susie" lobbied the Board of Aldermen for the right to wear pants during the Gold Rush-era, noting that she had worn "masculine habiliments" for twenty years previously, and wished to be protected against arrest for doing so.

Women were prosecuted for obscenity in the early twentieth century for wearing trouser suits — their sentences were less severe than in earlier times, but only because the Church was no longer able to enforce its views as strictly as it could in the Middle Ages. Prosecutions were brought in the UK, USA and Europe within living memory.

The photograph below is one is Dr. Mary Edwards Walker (1832 – 1919) an American feminist, abolitionist, and surgeon. She advocated health care, temperance, women's rights and dress reform for women. She was widely criticised and ridiculed by Christians for failing to follow biblical injunctions about transvestism. She is currently the only woman ever to receive the US Medal of Honor.

Prior to the American Civil War she earned her medical degree, married and started a medical practice. She volunteered with the Union Army at the outbreak of the American Civil War and served as a surgeon. She is the only woman to receive the US Medal of Honor and one of only eight civilians to receive it. She was frequently arrested for wearing men's clothing. Her name was deleted from the Army Medal of Honor Roll in 1917. She died in 1919 and was buried in her black suit. During the Second World WarI, a Liberty ship, the SS Mary Walker, was named after her. Many medical establishments are also named after her. Her medal was restored in 1977.

Even after becoming nominally secular in 1789 France continued to persecute women for wearing men's apparel, formalized by law. A law dating from November 1799, requires "any woman wishing to dress in men's clothing to obtain authorization from the préfecture de police". It was amended in 1892 and 1909 allow women to wear trousers "if the woman is holding a bicycle handlebar or the reins of a horse." Some départements passed their own laws criminalizing "transvestisme". The département de la Seine for example criminalized the practice in the early twentieth century by an arrêté préfectoral of Louis Lépine. Women in Paris needed to apply to the police for a special license to "dress as men" until 31 January 2013 when the law was abrogated by Najat Vallaud-Belkacem, France's minister of women's rights. Until then, police could arrest women for wearing trousers without a license, as they did frequently up to the 1950s.

Today only the most conservative Christians rail against women wearing trousers. A Google search on the topic of "Christian women wearing men clothing" will reveal a plethora of modern Christian sects holding the traditional line in the West. In the East, Orthodox and Coptic bishops also hold the traditional line. In July. 2014, Bishop Bishoy of Damietta and Kafr El-Sheikh governorates ordered signs to be put in churches in his diocese stating that “all ladies and girls above the age of 11 should refrain from wearing trousers, blouses or make-up during the sacrament of holy communion in the divine liturgy, and they should wear modest dress.”

Curiously, the prohibition on cross-dressing does not seem to apply to churchmen, and it is not difficult to identify a distinct enthusiasm for fashionable clothing and demeanour more usually associated with women outside the Christian Church.

Infallible Church Councils in the early years of the Church strictly prohibitted distinctive dress for Christian clerics, but somehow the draw of frocks, gowns and robes was irresistible. By 1215 these modes of dress were not merely permitted but obligatory.

High Churchmen seem particularly drawn to the extensive use of white lace, colourful fashionable gowns, girdles, and exotic headwear, especially in Catholic and Anglo-Catholic ("High Church") denominations.

Medieval Church dress

One cannot help but wonder how readers interpreted this
nineteenth century cartoon when it was first published.

Simple yet elegant modern dresses for fashionable young clergymen

Parading the skull of Saint Ivo of Kermartin in France
An opportunity to practice transvestism and necrophilia at the same time.

From 2012 Clerical Catalogues

A guide to Clerical Clothing for German Catholics

Orthodox Priests like these hit the headlines in 2014 for criticising, Conchita Wurst, a transvestite who won the Eurovision Song Contest. Their ire was drawn by the fact that Conchita was a bearded man who wore a dress, a combination that they seem to have found particularly offensive.