Late to this too, but such an interesting question!
Like you, I have a complicated relationship with feminine style. I've found that structured, ladylike tailoring works well for me, while floaty florals don't. And I do like a skirt. I think it helps to have a feeling for what dress shapes suit you.
Anyway, the new direction looks like it's working out nicely. I'm particularly impressed with the matching shoes and handbag.