At what point do you get rid of something functional?

I often keep things I don't really want because I'll keep using them anyway and I hate buying new things. At the moment I have several 4yrs old long sleeve undershirts that are too short in the arms, similar age sweatpants that I just don't like cause they don't have pockets, and a bar stool that a bit too tall and has cosmetic damage. The clothes I can donate but the chair is too damaged, it'd have to go to landfill (I'm fine with the damage but no one else will be). All of them have been not great for years but I also just don't want to just get rid of things that work