I don't quite understand how you can be expecting a pro-rec letter and only be "pretty sure" you made selection... If you haven't been explicitly told by your recruiter or your CoC that your package was approved, then nothing is for certain.
NEVERTHELESS, lemme help you put this carriage before the horse:
I think someone is being disingenuous with you. See, the boots you will
be issued buy at OTCN are actually real freaking good once you break them in, and will last you 10+ years if you take care of them properly.
That being said, and for what it's worth–– if you make it through OCS+NAMI with your aviation designator intact, you can expect to be issued a free pair of Brown Belleville boots after starting NIFE in Pensacola. These are all you will wear for most of your career in Naval Aviation, for the exception of certain watches requiring the NWU Type III (and whatever other working uniform you are expected to wear during your disassociated tour, should you choose to take your career that far).
I have personally recommended to multiple OCS-bound buddies now, to just buy any DOD certified
black leather 9 inch steel toe boots, found in
this publication, have them somewhat blackened and buffed (if not neatly polished) and throw them in a bag until it's time to wear them at OCS.
As for the watch...
Whether or not you'll be allowed to wear one during the most arduous part(s) of training (read: ass-whoopings in the sandpit) is entirely up to your class team, but most classes are allowed to keep them in their respective hatches to use them as alarm clocks, at a minimum.
So, just buy something that is inexpensive, but rugged, and that has a decently loud alarm.
