Also keep in mind that for a man, the watch is usually the only piece of jewelry they wear. Apple's Steve Jobs wore the same black T-shirt and jeans outfit every day. As I hear, Facebook's Mark Zuckerberg sticks to the same philosophy. Virgin's Sir Richard Branson wears the same white shirts and blue jeans almost daily. All of these are multi-billionaires that can buy whatever they want. If you meet a person with t-shirt or jeans and he looks well kempt, or you are such a person, the watch you are wearing is the primary accessory that people can evaluate to form an opinion about you, so that has to be chosen wisely.
The watches I wanted to wear in my 20s when I wanted to get laid vs. the watches I wear now are two different things. I'm now moving in circles where I sometimes hang out with independently wealthy people, and they do wear nice watches, and I have no doubt that they are real, as I've been to their multi-million dollar home, seen their high end cars, and been a guest on their 120-foot yacht. So if their watch wasn't genuine, I wouldn't suspect it, not in a million years, but it's still possible, if they are smart and put the 90% they are saving to better work and enjoy the same feeling with a 10% investment.
In the classic car world it's the same. People don't drive $20M Ferraris anymore, and rarely will you see a $1,1M Mercedes Gullwing or a $450K Porsche 356 Speedster in traffic. So unless you are in the wild where nobody knows you, picking a REP that you as a watch enthusiast *could* have afforded used is a smart move. At my age now, if I'm being complimented on one of my Panerais (my favorite watch brand), I often tell people that it's a heirloom from my late dad. That's a great line, that can really throw people off track as none of them knew my dad. Funny enough, I inherited my dad's Rolex Datejust with lots of patina that he, being middle class, bought new in the 1970s. I held on to it for many years, but eventually decided that there's no merit in having it in the drawer and sold it.