Still on the path to identify this shoe. I searched a variety of labels and it seems closest to an old brand called Taylor Made Imperial. Sole markings the same. Major difference is the beveled inner heel. no nails on the sole and three at the front of the heel.
I tried to play with the images to see if I could improve the readability and did somewhat. There is a partial name and part of a logo that I've traced.
Seems that the model is "The Grenadine" or "Grenadier".
If anyone recognizes the logo, let me know.