I think we were encouraged to use a thimble when we had sewing in our home ec classes - way back in 1955-1959! Plus my mother used one. So of course, I learned to use one, too.
Mom would flatten her thimble into an ellipse instead of leaving it round. Seemed to fit better then. She also taped the inside of another one to make it fit better.
I think I finally figured out it was easier - and way less painful - to push a needle through fabric with a thimbled finger than a bare one.