I finally am understanding what Jenn and others have been talking about with wardrobe essentials and then only adding a few pieces around them each season. I don't know why it took me this long, but I am finally having an "Aha" moment.
Maybe part of that is that I finally have something to dress for every day. For the past several years I was wearing uniforms to work, and in the very casual college environment. I was a stay home mom for many years. My weight has never been stable, so as soon as I almost got my wardrobe essentials in order, my weight would begin to shift again and I would have to start over.
I am finally seeing which items are essentials for me, figuring out which basics I need to stock up on, and holding onto a set of things in case my weight shifts again since that is my pattern.
I've been working on defining which items are essentials, and then coming up with a list of things that are missing or need replacing, as well as a few new items that I want to try for fall/winter.
It really makes so much more sense now, so thank you to everyone here that has shared their process and insights (and pictures).
I feel like for the first time in a long time I am getting my wardrobe in order and will be able to build on it going forward, and it's a good feeling!