I don't believe Deuteronomy 22:5 is talking about women wearing pants or button down shirts, it's taking about men and women dressing up to make themselves look like the opposite gender.
What about in your great grandfather's eyes?
I can tell you that when I was a child, women didn't wear pants to Church and girls didn't wear pants to school.
There are still many Christian schools that don't allow girls to wear pants. They do see it as girls dressing as boys.
Now back in the Middle East when Deuteronomy was written, I have no idea what men and women wore that made them look different.
Now men wear long hair and put it up in a bun. That and two ear rings.