Horological Meandering

I only own one relatively quite dress watch, but this is a question I like to ask myself as I browse some of the more imaginative offerings on this forum from brands like Urwerk, MB&F, and DeBethune. For those who own watches that could be considered "flashy", I'd be curious if you would share in what situations you wear them and when you avoid doing so. 

I work at a defense research laboratory, a more austere environment where it would almost certainly be frowned upon to wear these things. In this setting, very few people know anything about high end luxury watches. Wearing something like a gold Royal Oak here would come off as incredibly ostentatious, and it may even raise concerns during a security clearance interview. 

However, my main hobby is poker. In the world of poker, I would say that luxury watches are encouraged. They are quite commonly spotted at higher stakes games. On past trips to places like Vegas and Monaco, I've played against a variety of interesting characters wearing some very impressive time pieces. Most often, they are the typical sports watches like Rolex, AP, Richard Mille, Nautilus, etc.