I believe these are from the 1940s and the leather lining is in surprisingly good condition with no holes or overly worn areas. Otherwise, the outers are in very worn with cracking, the hole in left boot is in outer layer only, does not go through to the leather liner. The leather has been conditioned to prevent further cracking. Wouldn't recommend these for any serious use unless you have them rebuilt, but a cool piece of history to have for general kicking - these were very highly regarded boots in their day.