I've been considering an enhanced (to me) way of thinking about how to get rid of items that no longer belong in my closet (or at least move them to the holding zone), and that is to ask the question: "If guilt were *not* an issue, which items would I get rid of?"

Guilt about an item (how much it cost, how little it's been worn, realizing it wasn't as perfect as I thought because I purchased it in a hurry, all of the above, etc.) makes it difficult for me to cull it, but once I asked this new question, suddenly items I've been on the fence about were flying off my shelves.

Well, virtually, at least. I use the Stylebook app, and I created a section of my "closet" for just these items, and I have to say, seeing them all together (rather than just one at a time) makes me feel even more ready to get rid of them for good -- as if all of their collective inappropriateness makes it more obvious that they don't belong (whereas I can more easily justify keeping one item at a time).

I suspect that when I do the physical version of this it will be easier still -- piling them all in one place and letting guilt not get in the way!

Anyway, just posting here in case someone else finds it useful. Sometimes framing a question in a new way makes all the difference.