Nike Mogan Mid 2 JR WS Skate Shoe - Boys' - $35.97

If your little dude likes to go big on his skateboard, it'd be a good idea to get him in the Nike Mogan Mid 2 JR WS Boys' Skate Shoe. The mid-top collar provides support to help prevent rolled ankles from nasty falls, and the Phylon midsole cushions big drops so he can keep trying until he stomps it. - $35.97