For a Rolex, I think you need to somewhat act the part because there are so many fakes. Yes, I know there are many exceptions and you shouldn't simply judge a book by its cover but seeing a Rolex on your busboy is going to be a little more suspicious than seeing it on a guy wearing a suit stepping out of his porsche 911.
Most of my friends own at least one gen Rolex. No, it's not because they are all rich...but in my culture a watch is usually a gift that you get when you get married from your wife's family. Since Rolex is well known, 99% of the time, they get a Rolex. Most of the time it's a datejust but thesedays many people get Submariners. These high end reps are virtually identical to the gens (other than the pearl). I know that we like to nitpick about crown height, crown size, laser etch, slight difference in spacing/font of the dial or date wheel but this stuff is never known even by the guys who wear a gen every day and then wear one of my reps.
I have always been a "sensitive skin" guy so I don't like anything touching my skin. So I tend to wear loose t-shirts, loose pants, loose socks, etc. I also rarely use any kind of soap on my skin, cologne, deodorant, etc. I'm blessed to be Asian and rather hairless so I never have an odor problem or anything like that. I don't even wear a wedding ring. So when I got married, I told my wife's family not to get me the watch.
However, I have always liked watches. But since I rarely wear them except for special occasions, I don't feel it's worth it to buy a high end watch. In fact, I will likely lose it because on the days that I do wear it, I'm constantly taking it off and putting it down wherever.
But I do have a few rep Submariners, some Panerais, Cartiers, etc. I've never actually been questioned about them because everyone around me assumes that they are real. I've always driven nice cars (currently a BMW 750Li but MBZ before that, etc.) and when they do see my watch and make any kind of remark, I always just brush it off like it's nothing.
One guy at work a few days ago saw my latest Submariner and said how nice it looked. He even said that he knows it's not a fake because the hand sweeps.
When I wear my Panerais, most people don't even know what it is. Sometimes they talk about how big the watch it but that's about it. I did have a few friends ask "Is that like an expensive brand or something?" and I say "nah". I do like wearing the Panerais because when I do come across someone who knows watches, they usually get very excited.
If you don't want people to question your high end timepiece, don't wear a Rolex or Breitling, wear a Panerai or AP or any other less known brand. I used to say that about Patek but it's getting well known now.
RVD.