I've cleaned out a lot of shoes (off to Goodwill with ya!) this past year because they weren't comfortable. ANYTHING that isn't is going! It isn't worth my time to spend time in uncomfortable shoes.
Right now, I have three (3) pairs of comfortable footwear: a broken-down pair of Topsiders, a pair of Peto (?) shoes, and, believe it or not, a pair of Justin roper-style cowboy boots.