Ok, I've given this more thought and feel the need to document - thanks again LaBelle for creating this thread!
1. As mentioned, start judging outfits by how I feel first and foremost. This ties into Ornella's great point about: "prefer feeling 100% me at the cost of appearing uninteresting". CPC (casual polished classic) will be my 'style north star' so to speak.
2. Start buying only 8+ items ... I've got plenty of stuff and don't need any more. I notice that there are a lot of "meh" items in my closet and I don't think I need to add any more! To qualify as an 8, I must EITHER really need it, or really love it - preferably it will deliver both, making it a 9 or a 10.
3. Try more of Angie's ensembles - seems like a good rut-prevention strategy.
4. Try more neutral-mixing. I think this may be a way for me to up my style in a comfortable, easy way.
5. Pretty much everything in Ornella's post.
We need some sort of reminder tool to keep us on these!!!