I love these shoes. I wanted to have the laces tucked away as in the picture, but that ends up making the shoe somewhat loose on the foot--and even then it's still pretty solid to walk in. I've taken these to conferences and gotten compliments and I've also worn them to stomp around tourist sites, and they've been consistently comfortable. I did have an issue with the narrow space of the toe box generating too much friction with the seam of the socks I was wearing but that seemed to be an unusual confluence of events-- all the same, tl;dr: the toe box is on the smaller side. The feeling is relatively snug and generally solid (I have medium feet and fit most shoes). These are the classiest version of chukkas that I've found.