Clothes only get worse while being used (or cleaned). Thus, all clothes I donate are basically in a condition that I considered "fit-to-wear" just one usage ago. Is it a stretch that someone would be happy to get for free what worked for me just until now?

That being said, after reading articles like this some years ago, I started to throw everything that is actually damaged to the trash (even if it is only a small hole). Maybe I am overdoing it - but I totally understand the mindset of "worst case they will have to trash it in my place".