I also read this yesterday wehn I had no time/energy to digest, so am popping back now to comment. Not sure I can even do such a great piece of anazasis justice, but I do have soem random thoughts in my head that might help, so here they are... in no particular order.
1. Well, the first and most important thought is that you do need to rest assured that you have an amazing style. Just look at the photos you chose... no matter what they are illustrating, you look fantastic.
2. I hear ya on the winter thing, you know you have my total understanding and empathy.
3. I'm blown away that you wore those two sweaters 30+ times. I think that no matter how much I loved something, wearing it that much in one season would make me sick of it. So I think you should figure out what you liked about those pieces so much, and duplicate or triplicate, but in a different way.... so you get the love and function, but a different look.
4. It's hard for me to relate to the working at home thing, because I don't. And I'm still one to change into lounge wear the second I walk through the door. But I do think that wearing the same things to work in all day, as well as go out in during the day or the evening, would get tiring. I think the idea of a lounge capsule, that FEELS good might be worth persuing. Then when you get changed to do errands, or whatever, your casual clothes feel more new and fresh to you, not same old same old. I love the chance to put on jeans and a nice casual sweater, becasue it's NOT every day that I get to.
5. I know that for me, it's hard to have interesting basics. I seem to feel that if I have a basic piecs, they can't be too interesting because they have to go with everything, and in order to have the edgy piece or interesting piece, I end up with too much... the basic AS WELL AS the interesting. I need to get over this. Do you?
OK, that's it for now.. if I don't post I'm afraid I'll lose this!