that's a really good question. sometimes I do. my reps, and even my gens are better than my boss's.
I have one avid watch collector colleague and even my gens put his to shame i feel embarrassed to even swap my watch duties on a regular basis. I respect this colleague and would really hate to have his "feelings" hurt by showboating all my watches, reps or gens alike every week.
He did point out one watch of another colleague and made a sarcastic remark about it. ( the watch wearer was wearing and obvious fake pos) but I don't think my good colleague friend knew. He did know that it was a high end watch. when he told me he made a sarcastic remark about the watch, i cringed at the thought and didn't want to break it to him that it was a horrible rep. maybe i should have.
then again, i have another colleague of mine who has obvious gens where each one of them is worth as much as a car. I pointed one watch out that she had and she was taken aback that anyone even noticed, as she has since become self conscious about wearing high end watches around me. We shared some watch stories and told her about my gen Omegas and Rolexes, but didn't talk about my rep brands.
I sometimes wear my Citizen Eco Drive when i have meetings with my boss. He's the Director of the company, so yeah, you don't want to upstage him.
Right now, I've been wearing the same watch for two weeks straight. Just an ordinary Lumtec. Will switch to my newly modded sunnydale crystalled PO soon.
on the other hand. I proudly write with my gen MB rollerball pen and everyone knows I have one. I mix it up with my Narikaa MB fountain pen sometimes.