Yep, this happens all the time in our house. My husband is used to it by now. He would keep wearing the same old tired clothes until they fell off of him, if I let him. Once something goes out of style, or has stains or holes, out it goes. If it's just out of style, I take it to Goodwill. If it has stains or holes, it is thrown away. He really protested at first, but now he has learned to be grateful that I'm keeping him from looking like an idiot. Plus, he sees that I clean out my own closet several times a year, so it's not like I'm just picking on him. ;) Since your husband's jacket went out with the 80's AND it reminds him of his old girlfriend (!!), put it in the Goodwill bag with whatever you need to clean out of your own closet, and take it away. Will he even notice it's gone, really?