I wear my 6542 or 6204 daily. I've had pawn shops, jewelers and even the owner himself of a Rolex store compliment my watch and not question it at all. It all depends on you. What do you like? What 'fits' you, your age, your person? I'm 68 years old and drive a Mercedes. People don't question rep or gen. My son is 30, drives a Toyota. He gets questioned about his 116710 GMT or his 16160 Submariner all the time.
As mentioned, I am old and reps are getting too expensive for my tastes. As a young man a gen Sub was around $600 new. For me, building a watch is the 'best'. But that's why this place is so great. You do what you choose to do, what's best for you, and it's all right here.