I like to wear barefoot street shoes in the summer, allowing for natural foot movement. Stiff (winter) walking boots are from a different planet altogether. It was difficult to find ones where my toes don't feel constricted and crushed. These best fit the bill. The last is wide enough, and the toe cap reasonably big. Plus they keep my feet dry even walking through puddles. Only downside I can find, is that my heels start yearning a softer (gel) inner sole after a day of walking. In my experience, other stiff boots like this have the same problem, perhaps exacerbated by having learned not to step on the heel in the thin-soled barefoot shoes and zero-drop running shoes.