I (tried) to do same for my kids but in the end I bought both of them a new watch instead of vintage. But that’s more because of the fact that I simply couldn’t find the preferred watches made in their year of birth
Now mine were boy and girl that makes life easier. If two boys, then I would recommend you buy them both the same watch.
Which ones would I recommend or pick myself?
I would probably go for the submariner or the Explorer. Why? The submariner is Rolex, it’s indestructible it holds value forever and it’s a, (how to put it in today’s gender neutral environment) it’s a mans watch.
Alternatively the Explorer, same Rolex dna but more modest in presence
Depends on the character of the boys I would argue