An article (originally penned in 2015) by Gary G on Quill & Pad explored why the author had never owned a Rolex and how that might change. The article is well-written and the writer does not hold back when admitting his own biases. Others vow never to own a Rolex, which i can understand but not agree with.
Photo by Watch Pro Site
I own exactly two Rolex watches, a 14060M Submariner (my first expensive watch) and a white dial Oyster Perpetual 39 (a gift from my wife). Both were purchased before the more recent price hikes, the OP new from an AD with a one-week wait (!). Objectively they are the best all-around watches in my collection in terms of esthetics, comfort, ability to tell time, basic durability and timekeeping. At the end of the day, Rolex does make a very solid product at a very fundamental level.
Photo by Winding Ritual
Now I understand that one can argue they are never going to buy a Rolex in today's market where grey market dealers are the only ones with stock and asking double or more than the suggested retail price. I agree, they are not worth paying that much for. But you can find pockets in the secondhand market where the prices seem to be more in line with the actual “value” of the watch. A good example of this is the five-digit Datejust market. It’s a great classic model and with inflation the prices are somewhat reasonable.
Photo from Chrono 24
It’s also important to note that there is indeed a Rolex mystique that is tangible even though most people don’t even notice that you have a Rolex on. This mystique comes down to the very subtle tactile feel of wearing and Rolex. Even the rattly hollow end-link bracelet of the five-digit Submariner has a very satisfying feel as you secure the flip-lock mechanism on the clasp. It feels cheap but it honestly is the most comfortable bracelet in my collection. The modern one on the OP is amazing too, and I’d argue that Rolex has the best bracelets in the industry, especially with its identifiable taper.
Photo from Chrono 24
Let’s make it clear: If you only have a mild interest in watches, there is no reason to own any mechanical watches period. But if you do care about watches as a passion, experiencing perhaps the best ever mass-produced brand across categories is key. Rolex is undeniably an execution of a distinct vision that has become the most important company in the watch industry. Omega is fine and I love my Speedmaster, but all its technical achievements (many that surpass Rolex) do not make it a Rolex, and you know what that means if you own one.
Photo by Watch Review Blog
Also, I am not a fanboy, but I am far from a hater. I believe that as far as finishing and dial work, nothing beats Grand Seiko in the $5K and over price range. However, owning a Grand Seiko is its own experience, but nothing is going to dethrone my Rolex watches as the best all-around watch that gives me back the most pleasure.
Keep your eyes open and dig deep. You may be able to find your first Rolex at a reasonable price. Jump on it. But more likely if you are reading this, you probably already own one or more Rolex watches.