I dont live in a tropical region so I will admit that I dont know more than what I have read on this but...... If you step on a stingray, shoes or not I was led to believe that the barb was long enough to hit you in the ankle or shin, over your shoes. Even if it hits you where your feet are covered the barb would most likely still penetrate. Maybe I am wrong on this.

If I had shoes I would wear them regardless if out in the surf. Christ knows what else is there besides a stingray. Or I would stick to eating coconuts from the beach. As far as I know they wont sting or bite.

BTW. I watched that episode a few days ago on OLN and as far as I could tell he was wearing his neoprene dive booties every time he stepped in the water, even at night while torch fishing.