Another issue that I'm trying to deal with is that I don't particularly care for brogue shoes or wingtips of any sort. I Prefer the round toe type dress shoe.

I have a pare of shoes that are made from wool tweed, and they match that driving cap back there in the pic. The problem with them is that the sole is a little more like a sneaker. That is, the sole of the shoe has a lip that comes up from the bottom an inch or so. Other than that I like them as dressy casual shoes.

I guess I really don't know enough about shoes.