^I'm jealous, when I wear converse my feet start to hurt within an hour..
In the summer it's my Birkenstocks. Good looking? No. Comfortable? Hell yes!
In the winter I like either my Nike Jordans (high), great support even when they get older.
For some reason my feet are really bad at breaking in shoes. When the leather isn't soft to start with they will keep on bleeding for weeks not very practical (or motivating) when you're trying to break in new shoes..