Comfortable right out of the box and I imagine will be even more so after a few wearings. The fit was as expected with medium socks. Leather and stitching seems to be high quality. A few scuffs and scratches will make this boot look even better. Front loop is too small for a man's finger. Rear loop is larger but I can just barely get my index finger in it - but it does work. Nice rounded toe box looks good and is roomy. Lugged sole is medium soft rubber which doesn't sound like wooden shoes on hard floors and provides good traction on a variety of surfaces. Insole appears to be permanent but has sufficient cushioning. This is my first pair of ankle height pull-on boots and I expect to gets lots of use in both casual and work situations.