This is quite a hard statement to understand
I would look pre-owned IWC Omega Tudor maybe even Montblanc for something sportier. What I do like is Porsche Design’s older more vintage looking watch on bracelet — befits the image but I suspect isn’t quite his style. For something more casual I like Nomos. And then in the micro brand segment I feel Baltic is doing an amazing job and within the budget. If all the above doesn’t appeal to him ask him to shut up and buy a Rolex when he has the money lol.
Best
Gatsby