I also hate shopping, and almost no dress shoes are ever comfortable to me. My issue is slightly odd toes (the podiatrist I saw once confirmed that my big toes are thicker than usual) which means that shoes that other people find incredibly comfortable frequently pinch.

I found a pair of dress shoes in the last year that are AWESOME -- Alegria Mary Janes. They're also very supportive. They're carried at Schuler Shoes, so possibly worth a try. (They come in fun colors, which is also kind of a novelty. The handful of times I've had comfortable-ish dress shoes in the past, they were never FUNKY fun comfortable dress shoes.)