For me, it’s not about out-wearing my pay grade but about out-wearing my lifestyle.
Rolex, trinity, and above can put a target on your back in most metros. I make good money but live a regular life. Sure, social-awareness, insurance, etc and you can mitigate some of the risk, but needing to do all that is a bit antithetical to a luxury experience.
(Caveat: I don’t work in finance but do work a desk job. Most people here aren’t watch people and couldn’t care less about one stainless steel vs another. They’d likely notice and comment on two-tone or gold).
It seems like the rule of thumb in that case would be ‘loudness’ of watch rather than actual cost. So blingy, high polished pieces, two-tone, attention-drawing pieces, and of course Rolex.
E.g. I don’t think they’d bat an eye at a moonwatch on leather or a reverso. Or my favorite, on an Erika’s originals