Your Plebe's Team Leader will guide them around the entirety of Reorgy Week (they're not allowed to go anywhere on their own then) and will take them to all the issue points for their backpacks, computer, monitor, etc. as well as to the C-Store to buy folders, notebooks ... Like others said, I would not recommend buying anything major until he/she gets a fell for what they actually need. On A-Day, there is a SAMI (a major room inspection) so there's not much they can have or store until later on.
Some nice items that are definitely allowed:
- 1 US, state, or military unit flag for the wall,
- A family picture stand
- A comfortable pillow or blanket
- Journal/Diary to reflect on their USMA experience
- Bible, leadership books, Art of War, etc.
- Coffee Machine or a nice mug
- A nice mouse and a mousepad (they don't issue these and I highly recommend this as a gift)
- A fancy watch that they can use for the many formal banquets and balls at USMA
The point being is that your Plebe will figure out a way to get their calculator, pens, and folders that week before school starts. There is little opportunity for them to get the above list which is where you can help them out with a memorable gift.