I think it's more of a comfort/shoe thing for him. He wants to be comfy, but all he has are his dress shoes and his athletic shoes (which are grey and black with a bit of yellow on them). He meant to get some hiking boots but we haven't been able to yet. He's a little worried about looks despite wanting to keep his feet from screaming at him, and I can understand that. If you don't feel comfortable about what you're wearing, you won't be comfortable (mentally I mean).

We'll see, though