Suz, your post and thoughts help us all to evaluate our wardrobes and needs. You do an amazing job of staying focused while still having fun and allowing for the occasional wild card. You buy for your real life but remember to include items like your elegant new navy dress. You could probably take an office job tomorrow and have many appropriate outfits already in your closet.
I can see the wisdom of upgrading each season, especially with current footwear. I can't wait to see how you style your pieces this winter.
Be wary of grey jeans. I dearly wanted some, have bought some, and have been rather disappointed because they end up looking unpolished and dirty even when they are clean and unstained. In theory they seemed a perfect addition for a cohesive wardrobe. In practice, not so much. If you find some good ones, please let me know.