This tends to be the largest pile to deal with in my experience.
The next category to tackle is the Maybe stuff. This tends to be the largest pile to deal with in my experience. At this point, you’ll want to look through these items and pick out the pieces that you wear often enough but could use an upgrade. For example, I have a pair of linen blend shorts in a coppery brown color I love. They fit me well enough and I wear them regularly, but they’re not perfect. If they were a high rise short, they would be! But they sit right on my hips instead of at my waist. These shorts aren’t something I want to get rid of right now, so what do I do?