Globe Superfly Skate Shoe - Kids' - $24.98

Kids are fearless, so if they're going to ollie over stairs that are twice as tall as themselves, they should at least have plenty of ankle support (and a helmet). The Globe Superfly Kids' Skate Shoe is a high top style that features a hook-and-loop strap up top to prevent rolled ankles so he can get up after a fall and try it again. - $24.98