Back when I believed "Rolex guy" was a type of person, I did everything to avoid liking the manufacture. I assumed they were overrated, overpriced and far too populist. Maybe this is partly true - when you consider it wasn't that long ago when you could buy one for a couple hundred bucks, while now it won't be long before $10k only gets you a basic model.
But when it comes down to it, Rolex's popularity is pretty well-warranted. As a company, they have a mindset that takes both innovation and tradition equally into account. They're like that kid in the classroom that doesn't always jump to raise his hand, but when he does, he's always got the right answer.
Their designs change at a snail's pace, so owners don't rush to upgrade to the newest models all the time. This keeps perceived value consistent and makes buying one pretty much risk-free. Unless you wreck it, you can always get most of your money out. And yet, they've lead some pretty awesome innovations through the years: from things like the oyster case and GMT complication to surprising newer innovations like the Oysterflex bracelet.
Sure, the movements may not be the nicest to look at. But you also don't have to coddle them. Rolex watches can take some punishment.
So don't worry that buying a Rolex will suddenly transform you into some kind of horological Johnny-come-lately; the "Rolex guy." Buy one, as I did, to see if you like it. I'd be willing to bet it'll still be on your wrist a year later.