"Love this bootie! They are perfect for the variable Portland weather. I can wear thick or thin socks with these (perfect for my cold office) and they are holding up to the rain. They were totally comfortable right out of the box with no "break in" time. The sole is a little thinner especially at the toe than some of the other bootie styles out there (and dressier because of that), so I am am a little worried how well they will hold up to lots of city walking. Should be fine for someone used to walking in dress pumps or flats. I've had these shoes for about 3 weeks and have been wearing them a few times a week since then."