Is it sad that i was more interested in the better shot of his closet than his hurricane fit?
I'll second the stay safe.
My father worked on the Santa Fe RR as did his father before him.
However when he wore a wristwatch it was an Omega Constellation.
The pocket watch would be my choice although you should anchor it to the button shank and not the hole itself or put a heavy fob on that end and thread the chain through the button hole into the watches opposing pocket.