What is allowed for footware will in jail, what can I drop off for shoes or boots?

You should call the facility first before you do anything and see if they would allow it. In state prison, some states allow you to send shoes or work boots (or order them for the inmate and they are shipped in). In federal you definitely cannot. All extra footware is bought through the commissary. The pricing is very fair for sneakers and boots. The inmate would need money on their books to be able to acquire them.