This is just what I have been told by my OSO. You will be issued boots at OCS. The brown ones. One to two pairs, depending on how many they have in your size. So, females with smaller feet beware. You are allowed to bring a pair of broken in black boots if you wish. This was suggested to me, so that is what I am doing. I went to a military surplus and asked for a pair of all leather, speedlace, black combat boot. Nothing special. (Don't get jump boots) They killed my feet during Prep-weekend, but in the past few weeks I have built up some calisus, so that is helpful. The down side to the black boots...they are no longer authorized as of sometime in Oct. But I figured I would have an easier time breaking in the boots issued to me if my feet were already rough. I hope this helps. Good Luck to you.