The only reason Rolex owners have Rolexes is to show they can afford one. And they can't wait to tell you about it.
Parents that teach their children that successful people buy overpriced trinkets are losing an opportunity to teach their kids the difference between 'good enough' and conspicuous consumption.
A Rolex is signalling stuff masquerading as utility stuff.
The utility value of a Rolex is approximately $50 (the price of a half-decent watch that will tell the time accurately for many years to come, assuming your phone doesn't already do that for you). The rest is signalling value (and in the case of a gold one some intrinsic value).
I'm perfectly ok with you not seeing my point. In the end the guy with the jeans and the t-shirt is quite possibly a lot wealthier than the guy with the Ferrari and the Rolex. (Especially when they're not bought with cash.)