I'd add onto what smittie says, maybe someone needs to consistently dress up for a period of time, a couple of days a week for a month. If it's something you want to do, it just needs to become habitual and comfortable through practice. Then once your mind is accustomed, you can add it to the repertoire of looks, it doesn't need to be an all the time thing.
I think this is what I basically did two years ago, I went through a skirt wearing phase - often with refined shoes, and got over feeling 'too dressed up' running daily errands. Now I don't wear them quite as much for practical reasons, but when I do, I don't feel self-conscious about it, they are my clothes as much as jeans are.
The woman in the red dress is a good illustration of concept, but I'm thinking in real life the woman in the picture is a model doing a fashion shoot, so the gawkers are probably first and foremost thinking 'wow she's tall'