Dylan mocks not only women but young girls by parodying being a young girl when Dylan is an adult.
All this smells of entitlement, as if the Country of Women is just an uninhabited place anyone can take over or inhabited by primitives who need to be shown how to actually woman properly. And Dylan has no idea about how women and girls actually are, so all we get are stereotypes of the worst kind.
It's not how Dylan dresses, that's fine. It's that we are told that what Dylan is means is being a woman; that what Dylan performs is what all of us are, that there is nothing more to being a woman than clothes, makeup, jumping up and down with glee about some new makeup product of kitchen appliance and so on.
And it is THIS which is viewed as progressive now.