I agree that if you are trying to train him than making the clothes harder to get off will impede that goal as he needs to be able to get quick access if he needs to pee or poo.

Personally I would stick with the clear expectation that while it is ok to be naked in private that in the face of 'company' being naked is not an option ... so if you want to be naked you have to stay in your bedroom in bed during daycare hours cause it is not 'private' outside your bedroom when mama is working and if you want to be with the daycare and doing daycare things than you stay CLOTHED ... simple natural consequence to the expectation here is where you can be naked and here is where you are expected to be clothed ~ without punishment or reward.