I didn't bother. like uppercrust, I'm reveling in the joys of remote access
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.