I included Finds for most of the things I recently let go. Along with reasons.
Worn out and poor fit items are obvious candidates for editing. But I can be a bit more specific about the"style shift" and "just not working for me" category if you like.
With jeans, I'm getting rid of most of my low rises. I kept my Dres because the comfort factor is huge and I love them. I still have a pair of mid-rise Citizens (on their way out in the spring -- they have their uses now.) Otherwise, low waists are out. Higher waists feel more current.
Like Lisa, I'm trying to wean myself from skinnies. This is not easy given my former climate (her current climate). Even in Vancouver, I just know there will be times when they feel like the only practical choice. But I'm moving towards different cuts, so if a skinny was in question, I let it go.
For the rest, I pretty much asked myself: does this item make me happy? Does it help me make good outfits or do I always feel "off" in it?
However "nice" it is in theory, how is it working for me in fact? However much I thought I'd need it, what do I feel when I'm wearing it?
1. Kick crops -- I love how these look on others and hate them on myself. I tried, I loved in theory -- but, next!!!
2. Turtlenecks -- Angie made these a top pick last year and turtlenecks are a winter essential for me and these were in great neutrals/ colours for me. But I found them itchy and a bit on the thin side. Also the cut bothered me. I realized I wanted a snugger, more fitted look. Next!!
3. Everlane silk tops. Based on past experience I was sure these would be winners in my closet but something about them just didn't work for me. I still don't know exactly what was wrong. But I never felt good in them.
4. Kimono -- only wore it about 6 times, never felt quite right in it.
I do make intuitive calls when I'm in process. Most often in the direction of "edit it out" but occasionally in the direction of keeping something I'd been sure I'd get rid of.
I still have two or three items in my closet that I think should go. Debating those. They were pricey and I feel I haven't got enough wear from them to justify the cost. So it is harder to let go.