I do understand what you mean about the obligatory smile. I always got that as a child. I remember a man teacher telling me he would help me with my wood work project if I would just smile for him. I have found the whole idea insulting ever since.
Saying that, I do dress to flatter the figure. I always put on weight on the bust and stomach and the last thing I want to do is draw attention to that area of my body. Sometimes that means tricking the eye so the shape is more hour glass or skimming over the area. I feel more confident when I am dressed in a way that I find more pleasing for myself.
I really like the unstructured look though and live vicariously through others that pull it off. We have a Japanese girl staying with us and she always wears clothes that are totally unstructured with the white sneakers....totally suits her. I dont like the unstructured look on myself because I feel the whole bust thing makes me look matronly and its not a look i want to convey. I did once wear my pyjamas to a gig so I'm not always into looking conventionally aesthetic, but I do think I was trying to look cool.
