Shirley, I think many of us have been in this boat--you want to try something a little daring, and it can be really uncomfortable wondering what people will think. My first attempt at this was wearing some leopard-print booties to an appointment. I could tell from the expression on the person's face that she was shocked I was wearing such a thing (I regularly go to appointments to this person). That was kind of a downer. I was surprised that I felt so crushed. But she said I should show the booties to the receptionist, who was really into fashion. Well, the receptionist practically swooned over the booties! That was a huge boost. And that really taught me that everyone's ideas about what looks good are different, and it's OK if some people don't like the way I look. Wearing these kinds of things are what *I* need to develop my own personality, and so people will just have to get used to it.
I still have a problem sometimes with wearing things outside of my comfort zone, because I wonder what people will think of me. But it is getting easier. I think that for us to be really happy people in all areas of our lives, we need to be able to freely express ourselves, and fashion is one way to do it.