My husband has lost 20+ lbs (he was not overweight to start with) due to a food allergy, and on his frame, that means most of his clothes don't fit. He's a total clothes horse, which has been a source of irritation for years. But, that's neither here nor there.
We did a mini weekend trip for Father's Day, and he had very few shirts that fit. During that discussion, and the subsequent packing, I held up each shirt in his closet, and he would say if it fit. We pulled 30+ dress shirts (WHY that many!??), several pairs of jeans, polos, sweaters, etc out of the closet.
He has a mix of quite expensive brand names & then things like Costco shirts. I went through & pulled out all of the excellent/like new condition but not $$$ shirts & listed them all on Buy Nothing. I've had a ton of interest. I'll get those out of the house today or tomorrow, and then move on to the other items. I'll definitely list a few things on eBay, as well.
Our teens are with my parents, so I took the opportunity to also go through their rooms. I got rid of so much recycling, a bunch of shirts they have outgrown, school papers, etc. It was so nice! You can see their furniture again. ;-)