Masculine and feminine attire must be judged in the context of the revolution which roared through our culture in the 60's and 70's. Part of this revolution was the "sameness" of the sexes and the feminist movement equating women with men in every respect. Out of this revolution came the pushing of pants for women as skirts and dresses were discounted of all value and seen as "feminine" and therefore symbolic of oppression, subjection, and degradation of women. It was a vestige of the patriarchy oppressing women. Pants were a sign of female liberation. "We're just like men". "Who wears the pants in your family?" was an oft used phrase in the 50's, before the revolution. One of the things that had to go in the feminist revolution were all of the vestiges of male authority.
Ironically the feminist revolution was, at its essence, a rejection of femininity. They so devalued women's God given roles, talents, and place in society throughout Christian history that they made anything associated with motherhood, staying at home, raising children, and dressing feminine, and acting feminine, something to be deplored as vestiges of oppression. We can see today the desire of society to have hard chicks and soft guys. It is the plan of Satan to topple God's order. If God has ordained men as heads of the family, Satan wants women to head the family. God made them male and female, Satan wants no distinction. Therefore women must become like men and men like women. The ultimate end of this diabolical plan is complete gender confusion and finally homosexuality pervading mankind.
So the "pants" issue must be placed in it's proper historical and cultural context keeping in mind the recent societal and cultural history in America. If one becomes myopic and only sees pants as a piece of neutral clothing at this date and second in time, one misses the point and the recent historical implications this issue has.
Once you put this in proper context you'll see that ancient, medieval, renaissance and other historical examples as well as other cultural examples are irrelevant. Those examples are completely divorced from our particular time and culture and how it is just in the last few decades, we got here. Clothes today mean something and that meaning is tied to the unprecedented social and moral revolution we experienced that goes against all Catholic principle.
Those good priests, Cardinals, Saints (Padre Pio) who were against pants on women are not some mean curmudgeons who were simply not "with it" and wanted to deny women any form of freedom. These were wise and holy men imbued with a true Catholic spirit who saw what was coming and the hidden agenda behind these new fashions and styles that was directly opposed to the social order of Christ. They gave their warnings, but the devil has apparently boxed up these warnings and thrown away the key by spreading the lie that these views are "outdated", "closed minded", "trapped in their time" as he appeals to our love for personal freedom and freedom of choice.
It all goes back to the apple. "Who says you are not to eat the fruit of this tree? God? He simply wants to take away your freedom. You have a right to this apple. He knows if you eat it your eyes will be opened and you will be like gods!" And so it is today. "Who says God's plan makes man the head of the family? Who says you are any different from a man? Who dares to tell you that you really shouldn't wear pants? Men are wearing pants." In the end the devil tricks us into thinking its about power and freedom when it is really about nature and divine order. His methods worked then and they are working now.