I appreciate all the advice so far in this thread and wanted to share an update with you all. First, I lost my mind and bought 2 more Dior pieces - a trench coat and a reversible winter coat. I have never had nice coats before. I think I always thought they'd get ruined/wet/dirty anyway and never bothered looking at nice ones. And of course as I near my 50s I've realized that not one of my coats has ever been ruined so I decided to finally invest in them!
Then I went to a store in my city that was recommended by my very stylish friend. Nice boutique with stylists and tailoring. I got 3 dresses - Ulla Johnson, Tibi, and Studio Nicholson. Also got a sweater and skirt from a designer I'd never heard of before (Barena Venezia).
Both coats and 2 dresses need tailoring and I looked like a different person after the tailor had finished pinning. My top takeaways from this shopping trip (point which were all made already by others in this thread) are
--Fit is everything
--Hold your horses, don't need to buy everything all at once
--Your eye will appreciate clothes that appreciate you. I've always avoided dresses as "not me" or too fussy. BUT I look much better in dresses than in pants and now I have a newfound love for them.
Thanks again for all the advice! Will share pics when things are back from tailoring