I love a functional and tailored looking watch (and am fond of the decades of battery-free use I have had from 2 Citizen Eco-Drives), but that is my generation.
We had 8 USNA mids at the house for Saturday dinner. Not one wore an analog “dumb” watch; they had their phones or smartwatch. That said, they do not realize yet that going into classified spaces means parking anything smart or with transmitting capability outside the door or leaving it in your car for shore duty or stateroom for sea duty, or field operations, leaving it behind in some situations. A sturdy water-resistant G-Shock with desirable functions (alarm, etc.) or other utilitarian watch is the norm for no-smartwatch work situations.
“Dress watch?” A dying concept, is my impression, at this age. I have my mother’s tiny gold Movado on a gold link band. I can’t recall when I last wore it.
But if the cadet or midshipman wants one, what fun to shop! SA cadets and mids can shop online and log into AAFES (Army and Air Force Exchange) or NEX (Navy Exchange) or CGX (Coast Guard Exchsnge) or MCX, because they are in the DEERS system. I believe ROTC contracted cadets and midshipmen can do the same; I am a little hazy when they get CAC cards. The Exchanges are tax free, usually offer free shipping and have less than retail pricing.