Very comfortable. These fit comparably to Red Wing heritage, Thorogood and Wolverine 1000 mile boots. The Vibram Christy sole is grippy and provides great cushioning for working on concrete. The toe area is a bit out of the normal looking and makes my size 9.5 feet look larger than they are. These might look overly large if you have a large foot size. I find these to be much more comfortable out of the box than Red Wing, Wolverine and Thorogood. This probably due to the poron insole. The leather is supple and good quality.