Check out Doug DeMurro's videos on YouTube. He is an automotive journalist in Philadelphia who daily drove a Ferrari for a week or two a few years ago. Plenty of videos of him getting gas and someone asking him how much his car cost, what he does for a living, etc.

There's a more recent comparison video of him driving an Aston Martin, a more expensive and arguably much nicer car, but because it's silver nobody gives a shit.

Unless you are truly flashy (red Ferrari, diamond watch) typically nobody will notice. And to the Rolex point specifically, there are more non-Rolex watches that look nearly identical to the Submariner than there are actual Submariners.

A friend of mine has what I thought for years was a Pepsi bezel GMT II. I caught a better look at it randomly and it turns out it's a Seiko.