Hiya - I think your idea sounds great and yes I did it too.
When I was young, we were battered kids but from an affluent background; think straight A's, square at school, terrible haircuts, not allowed to choose own clothes. Fashion and 'look' was at the bottom of the pile of problems, but it did make me feel sad.
In early adulthood I was confused, had all sorts of different clothes and no real idea of how to make the best of what I'd got.
Then got into self help and therapy, and took on board the ideas - changed job to charity, met all these charity women workers who helped people who had been abused, and part of what we had to demonstrate was 'being a healthy woman' with her own sense of self. I saw all sorts of 'looks' at work - punky, Lagenlook, purple and red, big hair, tattoos, makeup looks at work, painted nails etc.
And also, you know when you find a good item somewhere random, and then the finds add up over the years? That happened.
And I did 'one in, one out' - taking the shittest thing that I didn't really like or made me feel frumpy or whatever, and out it went to the second hand shop, meaning my clothes slowly got better, with only good stuff to choose from.
The best thing tho was finding a haircut that worked. I have thick curly hair and I found this hairdresser who cut the back layers shorter and the front long, with the overall length being mid back, and all of a sudden I rocked a look. I learned how to take care of curly hair.
I remember being on the train in London wearing my best new trousers, a top and jacket, with hair looking good and bracelets, rings etc and these girls were checking it out and at last, I began to feel good about my clothes and look. But like you say, I felt weird being looked at, being 'that woman.' It took a while to get used to. But clothes and presenting yourself to the world as you are is important I think. I like to think that people can generally tell what sort of person I am, how I think, what political side I'll be on etc, from the way I look.
At 40, the world does need you to give of yourself, your true self, and show who you are. I think women really need to step up these days, more than ever. You don't need to factor everyone else into how you present yourself - ten people, ten different opinions right?
So what are you thinking of?
Will you immediately give away anything that no longer represents you?
And what will you do with your hair?
I have recently had a side shave! Can cover it up with masses of hair flicked on that side if needed, but love it!