Like when you go to the doctor and say "it hurts when I do THIS" and he says "Well, stop doing that"I’d really counsel avoiding any shoes it actually hurts to wear. Loafers can be very close-fitting at the point of purchase (on the principle that they will "give"), but surely not oppressively so. Tongue pads and heel grips can help a lot with achieving snugness. I also tend to wears loafers only when I’m not going to be doing a lot of walking, e.g. lounging around on holiday or sitting at my desk.