Hold off on boots until the "Boot memo" is posted in your portal. There are specific boots that you will be allowed to have. You should purchase a pair from that memo and break them in. DD reported that her boots felt great from day one, and wore them when hiking etc before leaving for Beast, and had no trouble. Regarding packing, USMA will also post a packing list that is very detailed..........What you HAVE to bring, what are optional items that you are ALLOWED to bring, and what you CANNOT bring. As I recall, it was pretty detailed. Also, if Bates low quarters are still the every day shoe at West Point, spend the extra bucks on the Durashock models, it is worth it, according to DD. Good luck!