I highly recommend this Umi shoe for kids. It's very padded and easy to get on/off thanks to the velco top. (I also have a wide foot and had I been able to get a 2.5 it would have closed perfectly) As it is, I can still do it up and have it hold, even being on the small side.
The soft leather linings and thick padding inside--and cushiony rubber sole outside--umi's Finn sandal will keep your little mischief-maker comfortably on-the-go. Its leather upper and contrast topstitching will give him a ruggedly handsome look, just like Dad's.