This question is a tricky one and one only you can answer. However, my rules for this would be to donate if:  It doesn't fit  It is uncomfortable in any way.  It doesn't make you feel a million dollars  It is old, worn, and generally done.  You don't love it! I would never tell my spouse what to wear, and I wouldn't expect him to tell me what to wear, so it's an easy one for me! Luckily my other half doesn't notice what goes in and out of my wardrobe, which helps!