Jen: I've just read your last few posts. You are doing excellent work in your closet, and I know the Keep/Purge is the toughest step (and I have some of that to do this weekend, too). I spent a decade relying on the "base of black, plus a pop of color" formula. I believe this formula can still work with modern remixing of the elements, but I wear it a lot less because I decided I was hiding behind it -- trying too hard to look smaller, always appropriate while adhering to a tight budget. I discovered I was ignoring my own taste preferences and was not having "fun with fashion." I'm still learning to let go of my old mindset and am trying to learn to take more risks and wear only what I truly love. I've realized some things along the way -- for instance, red pants don't make my butt bigger, then make it brighter (hee).
I say, ditch the belt and ill-fitting boots and suits. Keep the shooties and the black skirt, orange top and flyaway cardi-- these can be remixed to look fresher -- as Deborah so wonderfully shared in her photo.
I'd encourage you to take a few photos of your favorite items -- the ones that make you feel fab -- post these where you can see them and let them help guide your future choices.