12 Point Summary:
First, male and female clothing was distinct during biblical times. The passage from Deuteronomy saying that men should not dress like women and women should not dress like men must have made sense to the Israelites. They lived the Scriptures before they wrote them down.
Second, though men wore robes, women's dresses were distinctly different.
Third, during New Testament times, Roman soldiers did wear trousers, so pants were known and were worn only by men.
Fourth, for a very long time in the Church, men wore pants and women did not. This had become established within Christian culture as one of the main differences between men's and women's clothing. Only very recently has this difference been obscured.
Fifth, Padre Pio would not even hear the confession of women who wore pants.
Sixth, the passage from Deuteronomy specifically forbids unisex clothing. Even if some persons or many persons in ancient times dressed the same, Scripture is still true and must still be obeyed.
Seventh, when the Virgin Mary appears in apparitions, she is always wearing a dress, never pants. All of the images and statues of her throughout the history of the Church present her wearing a dress, never pants.
Eighth, when visiting the Pope or the Vatican, women are not permitted to wear pants. And they must wear a headcovering. When George Bush and his wife Laura visited the Pope recently, she wore a dress and a headcovering.
Ninth, some Protestant groups still retain this insight, based on Scripture, that women should dress in a feminine manner, should not wear pants, and should wear a headcovering.
Tenth, clothing is an expression of behavior and role. Even in our sinful society, clothing is still associated with roles, for example: police officers, judges, nurses, priests, nuns, and others wear particular clothing appropriate to and indicative of their roles. And one's clothing is also an indicator of behavior and attitude. For example, nuns who are obedient to the Church like to wear the habit, but those who are disobedient hate to wear it.
Eleventh, men and women are meant to have different roles in the Church, the family, and society. Men and women are meant to have different behaviors. Clothing is an indicator and expression of that important difference. So, the more important thing is the correct roles and behaviors for men and women. That is the main point of that passage from Scripture.
Twelfth, when a woman gives up wearing pants and strives to dress in a manner pleasing to Christ and Mary, even though the culture around her tells her otherwise, she will be blessed by God and her prayers will be answered.