I'm inclined to think that the people who felt this style to be comfortable have not worn other Timberland shoes.  I love Timberland because of their comfort but the chocorua is not one of them.  I find that the Chocorua are on the stiff side. This is disappointing.  Before, when I see Timberland shoes I automatically equate it with comfort but now I've learned to be a bit wary.