In Orthodoxy, there are clear rules that women are not recommended to wear men's clothes and are not supposed to be like a man. There is a similar prohibition on being effeminate for men. Deuteronomy clearly prescribes refraining from any kind of disguise.
To prove the correctness and expediency of the prohibition on the wearing of a woman's dress by a man, one can turn to the Old Testament, namely, the book of Deuteronomy says in verse 22: 5: “A woman should not wear men's clothing, and a man should not dress in women's dress, for he is an abomination before the Lord Whoever does this is your God. Also, the topic of the difference between men's and women's clothing was touched upon later by the Apostle Paul in one of his writings, which, by the way, are recognized by the official church as the true teachings of Christ.
The history of men's dress
During Old Testament times, the clothes of men and women had significant similarities and were almost the same, except for details: women's robes were longer, noticeably wider than men's, and were sewn from a lighter fabric. However, this does not mean at all that a man could wear a woman's outfit. Already in the time of Jesus there were “trousers” in men's suits: aprons that were wrapped around the waist and narrowed around the legs - long or short. Their purpose was very pragmatic: to protect the genital organ from injury. The woman could not put on trousers for objective reasons. This is how the formation of men's and women's dresses began.
Religion and life
The first sacred texts were not at all like scriptures, they were a set of everyday rules, something like "Domostoroi", and therefore it is not surprising that, for example, in the Torah, it is said about how and when a man should dress, how the woman behaves. After only centuries - according to historians - some of the texts were rewritten, religious dogmas laid down on the everyday canvas, and the female guise became "second-rate" like the woman herself, the cause of the fall, apostate. A ban on the ministry of a woman in the faith was spelled out (until now, a woman cannot hold the post of a priest).
Later, it was the pants that became the bone of contention for feminists, but this happened a couple of millennia later.
Joint decision
The rule of the Sixth Ecumenical Council, which says “We define: no husband should dress in women's clothes, nor for a wife in clothes typical of a husband,” is largely decisive in the question of a man's wearing of women's clothing and the attitude of the church to this, but it should be noted that this rule is not directly concerns the issue of everyday life, but about the penetration of pagan customs into Christian culture, various rituals and the prohibition on them.
In everyday life, the exchange of dresses was also condemned due to the struggle against homosexuality that had intensified with the arrival of Orthodoxy in European countries. It was not the connection of a man with a man that frightened the priests; the diseases that arose and were transmitted after intercourse were the subject of eradication. Texts appeared explicitly forbidding men to be effeminate and wear women's dress.
There is an opinion that the attitude towards trousers is an etiquette norm, and not a religious one. In no scripture you will find a prohibition for a woman to come to the temple in trousers, but it is said that a woman should not become like a man, she is sinful in essence, because the original sin is from her.
Now the canons of the Old Testament are not honored so seriously, because much has changed since then, and even the church itself has undergone changes. There are only recommendations on how to choose your wardrobe, according to which we can conclude that men should wear clothes tailored just for them.
People should be based not only on frightening laws and prohibitions, but on a personal understanding of what is the morality that religion generates.
The Orthodox Church is not so categorical, and there are no clear canonical statements about what should be men's and women's clothing, but, despite this, it is worth remembering that wearing inappropriate clothing has never been approved by the church and to this day is not considered worthy of an Orthodox person.