I've never been a fashionable boot person; they've either felt too clompy, or not sturdy enough, or were too impractical, or too ugly, but these seem to fit the bill.  The cushioning is soft enough that I can wear these all day, but they're sturdy enough to withstand snow piles on the sidewalk (though I plan to condition these with some leather oil to make sure they last).  There's just enough support in the ankles without feeling tight.  I'm slightly worried that the elastic will start to stretch out, with taking these on and off, but I'm hopeful I'll get 2-3 years out of them.