I'm really speaking more of the movie, as I'm not familiar enough with TOS itself or its fandom to comment there. To me, that is something that definitely should've been changed.

It makes no difference if a girl wears a skirt or pants in day-to-day life; I enjoy having the choice. But wearing a short skirt and heels in the military? No, that doesn't really fly with me. It's ridiculous and impractical. What if, God forbid, she has to run? Why would this relatively idealistic future-society which is supposed have absolved many of these issues cripple their female officers that way when we don't even do that now?