I took early retirement 1 year ago and am finally trying to clear out my clothes closet. I've already pulled out 4 kitchen trash bags worth of donatable clothing by doing the normal things such as eliminating what hasn't been worn in years and what no longer fits (for the most part). Where I get in trouble is with things that just don't look new anymore, but there's nothing really wrong with them. When I worked, a lot of my blouses and sweaters would develop pills--especially where they rubbed up against a desk all day (I have a pill remover, but it does a poor job). I have the same problem with casual T-shirts which not only pill, but also shrink in length (but can still be worn) and/or fade. If they were spotted or otherwise damaged, I would toss them, but I have a hard time tossing these less than perfect items even though I put off wearing them. I probably have at least 30 items that fit this category.
I'd like to hear where some of you draw the line on iffy items (including shoes). When do you finally toss?