Cool because:
It’s a Swiss made diving chronograph by a brand that’s not usually worn by rappers or gangsters.
Occasion:
For wearing daily, though not very suitable as a dress watch. Obviously you can also wear it for diving trips although it would be a bit of a shame to get it wet.
Where have I seen it before?
That would be the movie «Lucky Number Slevin». The watch is actually part of an important plot point so it features unusually prominently in 2 shots.