These are early production 595 work chukka boots. They are sort of a "missing link" between the 3141 work chukka and the more modern 595 Traction Tred chukka. The outsole is a cushion wedge, while the footbed is veg tan with a small bit of foam arch support, referred to as "cushion comfort insole arch".
The story with these particular boots is interesting. I had a pair of 595 chukkas with the poron footbed, but they were too narrow. Sold them and told myself that if a pair popped up in an E or EE width, I'd grab them. I found these on ebay and snatched them up. The seller advertised these as being unworn and in storage for many years, with only a few scuffs from being moved around over time. I did not realize that these boots were an early version of the 595, so when I received them I was a little disappointed. However, I started to appreciate them for being a sort of an oddball boot.
Break in has been fairly typical. Not easy, not difficult. I have worn these for only a couple of hours so far, but the footbed is starting to form to my feet. The edge of the upper at my ankles were uncomfortable and scratchy, but I took a wooden leather slicker and was able to soften them up.
I'm going to keep wearing these as-is, and possibly put in a thin foam insole down the road for a little extra comfort.