(These are not my shoes!)
We are all reluctant to let go of things that have a satisfying emotional value to us.
I confess, I'm one of the worst.
Being a "Jonesing Baby Boomer", I think I was heavily influenced by the generation before me who suffered from the depression in the 30's.
My mother kept everything, and passed that tendency on to her children.
I have always told clients who think they want to de-clutter but can't seem to bring themselves to let go of things, that there is always a way to make the clutter look better.And there is.