My favorite pair of casual boots are the pictured Chukka Hikers that I had custom made a few years ago by the Russell Moccasin Company. The company has been hand crafting hunting-inspired boots in Berlin, Wisconsin, for over one hundred years. They offer a wide variety of moccasin-style boots and shoes in an array of different leathers and finishes along with many custom options. They can even craft boots and shoes out of your own game hides.
To order a pair of custom boots or shoes from the Russell Moccasin Company, you must provide careful tracings of your feet along with ten different measurements of each foot. Deatiled instructions are provided on their website and in their print catalog. Once you submit your tracings and measurements, they keep them on file for ten years so that you may easily order additional pairs of footware.
My feet are wide at the ball, but narrow at the heel. Because of this oddity I often find off-the-rack shoes to be uncomfortable. Because my Russell Moccasin Chukka Hikers were made to the shape of my foot, fit and comfort are not an issue. And that is the beauty of custom-made footware.