I tend to not buy skirts/dresses shapes and patterns that seem more "girly". Ex. floral prints, anything with pouf, ruffly, that spreads. When I see women in these I have to confess I think they are the types who adhere more to traditional gender roles.
I have a few minis and short dresses. I have one work pencil skirt.
I think if a skirt is always going to be an implied historical reference to some people, I would prefer one that says "sexual revolution", "modern", or "professional" and not one that says "I'll bake you cookies and clean your house". It is more reflective of my personality and more true to my beliefs and goals.
That said, once it is in my closet (which means it suits who I think I am), whether I put on pants or a skirt on a given day? I don't give it much thought.