My dad was a farmer and wasn't one for evening wear. Ha! However, Mom made him a bathrobe, and the occasion for wearing it was when out of town children and grandchildren arrived in late at night for overnight visits. So our memories are of being greeted by him in that bathrobe when we arrived.
After Dad passed away, I helped Mom sort through and give away his clothes. When it came to the bathrobe, I took it and still wear it. It wasn't worn out when I got it, but it is getting bad now. Plus one pocket is gone, because I used it in a label for the quilt we made for Mom with the family names arranged in crossword style.
I guess my advice would be to not make any quick decisions, think about what might be salvaged from the item and used in something else, and if you do discard it, don't look back. The person who owned and used the item is in your heart. Just cherish the memories.
Now I need to do something with the rest of the fabric (black and read plaid) that might become part of some keepsakes.