Originally Posted by Paul

If he had a legitimate medical reason for not wearing his proper school shoes since April then surely he or his parents would have told the school this via letter?

This to me makes it seem like he had not informed the school of any medical reason why he couldn't wear his shoes and the only reason why he hadn't been told to change them till now was because they looked like shoes from a distance.
It's not as though the school doesn't make it's pupils aware of the uniform requirement http://www.temple.medway.sch.uk/uniform.htm