It's a comfortable shoe. You can tell pretty immediately that its a thinner cupsole than the Wino Cup, its not quite as comfortable as that shoe but its still pretty comfortable. Its a bit narrower than the Wino as well. Neither of these things have been an issue for me, and when it comes to skating them I prefer the slight snug fit over the Wino which sometimes feel like my feet move around too much inside. I wear these to work daily but I'm not on my feet all day. I love having a casual looking shoe that I can hop on a board with spontaneously. I don't use these as my main skate shoe for planned sessions, but I feel like I could if I wanted to.