Cole Haan

I have really fucked up feet (large and narrow, multiple broken bones in random spots, bursitis, and now lymphedema) I swear by Cole Haan shoes. Think classic dress shoe styling with sneaker bottoms. Lightweight, cushy and supportive, and the leather is pretty good quality. In the "Key Features" section of each shoe, look for "responsive cushioning" - that's the thing that will give him the most comfortable and supportive shoes. I swear these loafers feel just as comfy as my own Hokas.