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"Very comfortable right out of the box. The padded tube things that are just below the ankle give great support and comfort, and are what makes this shoe really superb. They dip down below the ankle, so there is no breaking in there. The workmanship is first class, which I expect from these shoes. I got the white ones, which look good. Not a running shoe, not a dress shoe, but good for everything else office, boat, bicycle, hiking... I tried some that cost hundreds of dollars, but they were either uncomfortable or fell apart too soon. One pair got squeaky. These shoes are relatively expensive, fit exactly right, have perfect arch support, are comfortable with no break in, lightweight, and stable."