This is my first pair of Caterpillar shoes. I purchased them 10/15/12 from Gordmans.

The first thing to note is they are sized 1 size smaller than all other brands.  (10&1/2 equals 11&1/2..etc.)
Second, there is no break-in period with these shoes. They are the most comfortable out-of-the-box shoe I've ever tried on. (this is what sold me on them)

After about 13 months of wear, my right sole started ripping at the stitch starting to exposing my foot. My left shoe has no issues. I've continued wearing them for 4 months (until 4/1/13) after the rip started and now the whole inner right sole is ripped out from the front to about the middle of the shoe.  The comfort level is still there, but they have become unwearable.  (my left shoe is still fine)

Typically I will wear this type of shoe 3 to 4 years as they are used primarily in an office environment with a low amount of abuse.  These shoes have lasted about 17 months so I'm a little disappointed with the durability. Given my experience, I do not recommend these for anyone wanting a durable shoe that will last.

I recommend these for the person looking for a very comfortable shoe they will wear once in a while.