I know that for me, I'd need something more open-toed that the vans... just because it's too hot for that up here in Summer.
I'd just find some casual, comfortable sandals. They're everywhere in the smaller sizes... I'd try a good kid's shoe store and get him fitted. They'll no doubt have something!
Kmart have them the same as the ones in your first pic. From a size 4 for $15. I think target also had them.
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