Of course, when I go to a meeting I'm aware that perception matters, and in certain contexts there's a good chance I'm going to meet somebody wearing a nice watch who might make judgement about me based on what I'm wearing (human nature sucks sometimes). So I'm not going to turn up for a pitch wearing one of my Seikos (even though I love them) because they're probably too affordable and, frankly, too casual (Orange Monster anyone?). What I need is something classy and relatively refined without being flashy or ostentatious. Eventually, specifically to fulfil that role, I bought a used Omega Seamaster (which has become just about my favourite watch because it's so versatile).
I'd certainly think twice about wearing a Rolex for a pitch because there's always the risk it might make you look expensive, but I wouldn't think twice about wearing the same watch in a social context. Why? Because I love a good timepiece, and since none of my good friends are into watches they never notice what I'm wearing anyway, so I can get away with anything within reason. (Btw, I'm talking about stainless steel models here; if you're talking gold that is a different matter because just by its very nature it's attention grabbing.)
for the same reason, I wear modest watches to client pitches. too pricey they'll assume we are making out better than them and thus we won't be enforcing the "clients first" mantra. The same also goes for hotels. When I travel to clients and they ask where I am staying, I'd be a fool to say the "Four Seasons". If you stay at the Marriott, they assume you product is priced fairly.