Well, you don't buy a Rolex because you need a watch to tell time accurately. It is a luxury item.
You're really not selling this
What you're basically saying is that nobody should buy a Ferrari because a Corolla will do the same job.
If that was true I would absolutely be saying that. I am in love with the idea of owning a Lotus Elise some day, however if I test-drove one and found that it drives just like my Mazda 323 then I absolutely would not buy it, or if I found another car that is pretty similar to the Elise in most important respects for half the price, I'd consider going for that instead.
The nicest watch I own is a $250 Citizen (that I NEVER wear)
What's the point?
but I'm kind of toying with the idea of buying a nice watch. I work with a guy who wears a $5,000 Bremont every day and I find myself admiring the quality and look of his watch.
If the watch hypothetically didn't have a brand name on it (just to get "ooh, brand name! Add another zero or two on the price!" out of the way) and I thought that it looked like an unusually nice watch, then I might consider it (assuming the watch was any kind of price I'd consider paying). $5k for a watch however screams status symbol, and 'status symbol' screams 'pointless waste of time' IMO.
Think of it this way, what does a $200 watch (or a $15 watch) say about you?
Absolutely fuck all. People buy status symbols because they think that by having one somehow means something, however it does appear to carry weight with other people who buy into status symbols. A lot of people buy status symbols to imply that they're better off than they actually are.
If I saw someone's watch and liked it, I might say "that's a nice watch", regardless of price. How would I know how much it costs, unless they go full-chav style and still have the price tag on it.
I'm only thinking of replacing my ~15 year old watch because the finish is coming off to reveal a copper colour metal in places and I think it looks quite shabby