JMO he is not barefoot is he? My AH wanted $35 for tennis shoes and I told him to think about it. I broke down and sent $50 for his birthday and he got other things he needed worse. He is in his 6th month of prison rehab and sounds like a new person.
I guess I will not make some happy but if it was me I would send him the money if you could afford it. Hopefully he will spend it wisely.
Shame we can no longer send shoes into a prison!
Take care and do what you think is best.