jleno
1978
Okay, I've been thinking about this a bit more over the past few days.....
I've compiled some of my thoughts below, feel free to comment! Keep in mind this is just for fun and I welcome disagreement 
Watches at work:
Best case scenario here is if you work in the luxury watch industry. If so, I think this is perhaps the ultimate carte blanche to wear just about anything in any setting, even outside of work.
In more general work environments, I think the rules are very nuanced depending on what the industry is, the nature of hierarchies that might exist in the workplace, and the process by which money is made. Professions in the luxury industry will have higher limits as to what can be worn acceptably. But outside of that, it becomes more difficult. Almost any CEO, whether of a small startup or large company, must project restraint (at least in public) to avoid pissing off both employees and investors. You almost never see people like Musk, Gates, and Bezos wearing anything that could be considered ostentatious out in the open, even if they own private jets and mega yachts. Tim Cook obviously has to wear an Apple watch. On the other end of the spectrum, lower-level employees should fear incurring the wrath/jealousy of their bosses as well. I would think those working in finance, medicine, and law may have some higher limits on what would be considered acceptable, but still subject to rules of hierarchy and in appropriate settings.
For professions with little or no workplace hierarchy, luxury watches of any type should usually be no problem. Actors, musicians, and athletes can wear anything as they do not have the same nature of employee/boss/investor relationships that more conventional jobs do. In some cases here, I would go so far as to say a little flash is encouraged. Anyone running a sole proprietorship or working alone (e.g. day trader) may fall into this category. Basically, any job where people cannot guess your income and a frugal lifestyle could be interpreted as lack of professional skill/success. In these instances, I would imagine there are no consequences if you want to ball out to the max, so even the most audacious of "f*ck off" time pieces are fair game.
Places where watches require a larger degree of restraint than most include anywhere they may be associated with corruption. I mentioned the defense industry in my case, but I think politics is a better example. More basic Rolex and Patek could be fine here, but there's definitely a line of acceptability that should never be crossed. I'm pretty sure that if Trump was ever caught wearing an RM erotic tourbillon, CNN would explode. There are also some positions of extremely high power, responsibility, and/or moral authority where I think any luxury watches should be avoided all together. Supreme court justices, high-ranking military officers, and anyone in a religious profession falls into this category. The traditional religions however. Anything goes for the "fun" ones like scientology, satanism, and sex cults.
Outside of work:
Flashy luxury watches are of course going to be far more acceptable outside of work, especially in recreational settings. Here, I'm more curious to know if there are any interesting situations or hobbies where people usually see them. Poker/gambling is where I've typically encountered them in the wild. I would suspect they are more commonplace among fashion and car enthusiasts as well. Expensive hobbies are generally going to be a good way to surround yourself by people who will not be offended by these things. Maybe the only rule here is don't go about wearing anything that looks too expensive in places like Detroit, Somalia, etc...
