I work in a professional services firm, no one is going to bat an eye and/or notice if I go through a different Submariner every day. I have no qualms about wearing my Subs, GMT II, Omega, PAMs etc in rotation. They're a dime a dozen at my firm.
But if I were to wear a $15k+ watch, that might attract notice. If I were to slip up and wear three different ones three days in a row (HBB, AP Diver, 6263--it's easy to do!) people might start asking.
Would it hurt my career if I was known as that guy who owns a bunch of expensive watches? Or that guy that owns a bunch of fake watches? Probably not, but on some things it's better to just fly under the radar. I'd rather be known for the quality of my work than what watches I wear.