I saw this post a couple of days ago and knew it would require more brain power than I had at the time, and I'm so glad I waited. What a wonderful post by you Emily, so well articulated. And such well thought out responses as well.
I'm not sure where to start, I could relate to so much that you said. I wish we could sit down over a coffee and properly hash this all out.
So, in no particular order...
Agree totally with the mix and match thing being a lot harder than it seems like it should be. Whenever I've tried to do a capsule for travel, or to play along with a Vivienne file theme, or a YLF challenge, I seem to default to my "boring" clothes, because they are the ones that mix and match the best. But this doesn't make me happy. Yet when I add in something interesting, the whole minimal idea blows up. Doing this well is tough, but probably worth the effort.
I think you should try to track ALL your wears... even if you do change multiple times per day. This is the way to keep your needs REAL. And maybe if you see that you wear your scrubby fleece sweater every day, you'll be able to give yourself permission to buy a nicer fleece sweater, or a nice graphic sweatshirt...
Have you thought about patterned bottoms as a way to add variety? Esp if you have several solid tops. It can be a tough first step, but they don't need to be outlandish, esp if you look for dark patterns, like black watch. I'm still kicking myself for not getting some black watch jeans several years ago.
I also relate to the polished but only so polished, and struggle with this daily. I am polished by nature, no question about it. However it's really easy for me to end up feeling too polished, or precious, without really trying. It's pulling in the edge, or casualness, to downplay the polish, that I need to feel authentic, and which is my major challenge at the moment. And explains why I struggle more with dressing for work, when the clothes themselves tend to be a bit more polished... without the casual element I go into polish overload.
OK, gonna post this now before I lose it - and I need to get on with other things. I may be back!