Sorry, I didn't really read your original post and thought you were asking what watch to buy him to bring TO basic training, but we can still keep it in budget and send him to basic with a nice watch AND once he graduates get him something a lil' dressy.
I'd get the aforementioned AE-1500WH black band/regular face combo to send him there, and then pick up an Orient Bambino for a blues/dress watch. They're affordable, great looking, and are generally looked at as (arguably) one of the best first dress style watches someone can pick up. I have the model pictured but with the "pearl" face and blue indicators, I think the white would go better personally but the pearl faced version is awesome looking as well.
Orient Men's '2nd Gen. Bambino Ver. 2' Japanese Automatic Stainless Steel and Leather Dress Watch https://www.amazon.com/dp/B01N45HWRM/ref=cm_sw_r_cp_api_glt_fabc_7QR2MP36CMXTWNMD6849?psc=1
Try this. I’d also take a look at the following brands. Citizen, Orient, and Seiko
After a couple days lamenting over dive watches, I think they're not my cup of tea, even though there are some fantastic options in the sub-300 category.
That being said, I'm looking for a simple, large (42mm+) automatic watch with a reliable movement and roman numerals (or no markings) to last me ~5 years at least. My current watch, a Fossil ME3099 died after close to 2 years. I figured I should get a watch with a more reliable movement now. I recently purchased an Orient Bambino 2nd Gen Ver 2 but will be returning it since it looks kind of small and awkward on my 7.5 inch wrist. I found a Seiko Presage SRPC79J1 that looks fantastic but there aren't any Amazon Prime option available for me to buy, and return it in case I don't like it (which is why I'm turning to this thread here).
So basically, I'm searching for recommendations for an everyday dressy-type of watch to rock with a Nato strap.
Check out the Orient Bambino
This was my first automatic dress watch, but for a few reasons--none of which should deter you--it doesn't see much wrist time these days. Working from home has been the key factor--I used to wear this watch about every other day--but it's also a bit bigger than I'd prefer.
It keeps great time, and the crystal is blemish free. There are some miniscule scuffs on the case back which I can't explain. You can make them out in one of the photos. I'm also including the band the watch came with, but you can do better. As you can also see in the album, it hasn't aged well, but it was never much of a stunner; "genuine leather" is a travesty.
Here is this watch's Amazon page from which I've plucked the below details: https://www.amazon.com/Orient-Bambino-Japanese-Automatic-Stainless/dp/B01N45HWRM?th=1
Domed mineral crystal
Domed dial
Dial: white
Japanese-automatic Movement
Case Diameter: 40.5mm
Case Thickness: 12mm
Water resistant to 30m (100ft)
I'm asking for $75 including shipping. Venmo, PayPal, or Zelle. This is my first sale through this subreddit, but I've been a lurker and occasional commenter for a while. I'm also happy to chat over the phone or via video if you'd like.
Photos and timestamp: https://imgur.com/a/JTfanBz
Timestamp alone: https://i.imgur.com/UZlatUD.jpg
While not exactly what you’re looking for, this Orient Bambino is an option.
I really like the pen btw, if you want something that is similar, I would recommend looking at Mother of Pearl dials like this Sinn.