In developing your style, have you done an exercise like the "mood board" into-mind describes?
http://into-mind.com/2014/02/28/mood-boards-2-0/
This weekend, I finally pulled the trigger on a footwear purchase which feels like a big step toward loyalty to my own style. And it's giving me an injection of confidence and desire to get the rest of my essentials lined up.
I'm willing to go through constructive exercises, just not sure which ones are really helpful.