This is all useful information Una! I don't know that you need to be any more analytical than this, you've very clearly established several things that are and are not working for you.
I nodded along to many of your work musings, especially re non-sweatered tops, unworn jackets, and a desire for interesting professional pants. My own musings for myself regarding the first two are that 1) I don't like wearing sweaters under my non-leather jackets, therefore all my sweaters need to look best as stand-alone tops, and 2) I really need looser blouses to wear under my jackets AND that means my jackets also need to be looser and longer (most are more on the shorter and fitted end). So basically I realized that I need all new blazers, which is a little depressing.
Why not wear your silk button-ups under your jackets? Too corporate looking? I love wearing my (very few) silk shirts with my jackets, they are pretty much the only thing I have that I can wear underneath and I wish I could afford a few more. And why are your leather jackets not getting worn? That seems an odd one to me.
Regarding the work pants, I've slowly been collecting interesting trousers but most of them are more summery. I just can't seem to find good wintery trousers like the ones that Angie posted! And when I do, the fit is always off. I share your frustration with this one, hopefully we can both find something good this season.