I am the type who I don't leave the house without makeup, yes I know I am a dork that way. But I will even put on makeup to mow grass, I know I am going to sweat it off, but I feel better when it is on! Hair yes it is done too before I go outside. But clothing, I would just wear jeans and shorts most places, but we never went anywhere I needed to dress up, other than when I went to work, and that is just on days when we have big meetings or school administrators here. Most people wear jeans to work which is VERY nice. That is something I am trying to do as a bit of a 180 is dress up more often when I didn't have to. People at work have commented on it, so it is noticeable.
I don't think OW ever dresses up, from what I can remember she doesn't seem like she would, and at the store she doesn't need to.