We got three trash bags of hand-me-down from my Aunt the other day. But first I made the ADHD pre-teen go through his clothes. He pulled everything out of his drawers and decided if it went into the Stay basket or the Go basket. This is my child who has trouble letting things go. He did great this time. I only nudged him a little. He made the decisions.
He is doing better about keeping his room less cluttered. It may help that the room is bigger, but there are not as many trinkets or treasures lying around. (Oh yes, Mom does not walk by his room on a daily basis in the new house. That might help also). Maybe the "Clean Sweep"-style room emptying sessions we perfomred every couple of months taught his some things. A Mom can hope, right?