Hi there! It would also help explaining what you did because it's not so obvious in each screenshot :p
The pants taking in the spot of a dress is definitely a bug - did this happen when you deleted an item? At least, that's what I think happened; you deleted a dress, and these random pants showed up instead. Did you ever close the game without saving?
Overlaying errors however is just something we all have to live with. If shoes overlapped pants, it would still look weird because not all shoes perfectly overlap the width of the pants, and vice versa. if you want something skintight and tucked into shoes, go with legging instead, since they're below shoes :)
And if you want the skirt to overlap the top, you're going to have to turn it into a dress instead - otherwise tops will always overlap skirts.
You definitely earned quite a bit of money!