I used to buy reps that I theoretically can afford. Breitlings, IWCs and Panerais. After a while... I just didn't care anymore. My rep collection now consist of vintage Panerais (sf240s and a 202a) and 3 vintage rolexes (gen market value of about 20k each). I came to the realization that 99% of the general population don't know of i was wearing and the 1% that knows, dont care.
Just wear what makes you happy, the people who pass judgement are probably not worth you time anyways. Having said that, I make it a point to wear a non-descript <40mm watch when I make a client visit, a tudor MC or a Rolex 6542 most of the time. To me, its not the value of the watch, just making sure that the center of attraction is not whats on your wrist. Its about the right watch for the right occasion for me....