Too much ankle in the windsor smith ones, sperry topsiders are almost flawless in design and there aren't many boat shoes that look better/more timeless. This is no exception. Don't wear socks with them, thats like wearing a shirt under a singlet. It can work in some (very rare) instances, but I wouldn't do it. There is a "Should I or shouldn't I buy?" thread here
but I take it you already know this. Wonder if we can get some more opinions on boat shoes here, while we're at it.