Son -- '22 grad -- best friend had the cheapest, digital Timex that looked like it came from the 1970's. For Christmas Plebe year we got him a G-Shock. He kept that danged, beat up Timex all four years and my guess is still has it on at Aviation School. Do not use a watch that needs charged daily. Your second day in the field, useless.
I"d recommend a cheap watch just because so many get damaged during summer training. During the academic year, things are different. They also sell a watch at the cadet store that will work well and isn't terribly expensive.
My son loved his G-Shock with multiple timers for land nav segment. You just cannot have a “smart watch” or anything with integrated GPS or internet access capability. He has a couple other watches for classes but always resorts back to the G-Shock for FTX or summer / “smoke sessions.” Just another note: Several past ‘ present cadets have made “most important items for BEAST” or “wish I had at BEAST” videos on YouTube. Some of these were very helpful when used in combination with the Academy list they send out.