Way to go, mo!
I just love more stories of how to be PPP--I am a slow learner, too.
I think it takes a vision and a belief that really great style is attainable for ourselves. Not a hallucination, but a really crystal-clear vision of what we think we ought to look like in a certain top, pants, outfit or whatever and a belief that we can look fab in the right clothes. I don't by any means have that nailed down, but I'm getting better.
I had to stop thinking of "I should have a brown jacket to go with my print skirt" and think, "if I find a brown or tan jacket or topper that highlights my ___ (insert best feature or style goal) and really makes me look wow so I can't wait to put it on and it goes with skirts a and b and pants c, then I will buy it. "
Passed up a brown linen safari-type cropped jacket this week that was so ALMOST what I needed but just...not. It was wearable, it fit almost right, it seemed to have the right length, pockets, my style type---could this be the one? --but in the mirror it just did not go wow. In the same vein of what suz said, I had to have a conversation with myself that this would not be the only item I would ever find. I could see myself wearing it but not just tickled pink every time I did, and I could see that I would still be on the hunt for something "better".