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How To Buy Your First Rolex

We help you navigate one of the most important decisions you’ll ever make.

First up, congratulations. You’ve clearly made it in life.  Or maybe you haven’t but you’re on your way and want to start the journey with an impressive timepiece that personifies your aspirations. Whatever the situation, nothing quite spells success like a Rolex on your wrist.

For those of us without a trust fund, procuring your first Rolex isn’t as straightforward as, say, buying a new suit. Some of you are even wondering if Rolex is the right name to bank on for your first serious timepiece. If you need more convincing, read this. Otherwise, here are some things to bear in mind when you’re ready to go shopping: 

This may seem like a no-brainer but we have to say it anyway: Always buy from an authorised Rolex retailer if you're getting a brand new watch. You may be tempted to head to unlicensed shops in the hopes of getting a lower price. We’d like to stop you right there now. Rolex prices are controlled so these shops aren’t likely to offer you anything significantly less. If they do, you’ll probably spend the rest of your life wondering whether you bought a counterfeit.

Also, only Rolex retailers have the equipment and know-how to give you advice and help you maintain your timepiece properly. And when you’ve invested a substantial amount of money into your watch, you’ll want to hold it to a high standard of care and maintenance. These authorised retailers will do that for you. 

Now this is really something you’ll have to decide for yourself. Do you want to spend under 10 grand? Or are you willing to invest a few more Gs into a watch that will double up as a family heirloom? In case you’re wondering, both are possible. Expect to fork out about S$7,000 for an entry-level, no-frills model. But know that even the most basic Rolex has a hand-assembled in-house movement and comes from the hallowed halls of one of Switzerland’s most well-equipped and high-tech watch manufacturers that operate on a mind-blowing level of precision. Oh, and they also have a foundry that makes the gold for all their timepieces. Really.

The interesting thing about Rolex is that the models all feature the same sleek, stylish aesthetic and don’t appear vastly different from one another. It’s a look that works. Even the sports versions are classically elegant and would be equally attractive on a skipper as on a businessman. But if you think that limits your options, you’d be mistaken. The difference is in the details—dials, links, materials, gems, and of course, movements.

Arguably, the most popular Rolex for men is the Submariner (above). So if you’re looking for affirmation with your watch, this would be a very safe bet. Of course, it also means you’ll blend in with almost every other Rolex-wearer in the CBD. If you don’t mind that kind of thing, it’s a great first Rolex but isn’t exactly the cheapest. For something less sporty and easier on the pocket, the basic Oyster Perpetual (below), Datejust or Air-King are your best options. These are all available in steel as well, which should knock some numbers off the price as compared to a version in gold.

Ladies, don’t go crazy on the bling because a diamond-encrusted bezel is less versatile and, needless to say, will cost more. A classic Lady-Datejust is a good starting piece if you like dainty dials. Otherwise, go with a regular Datejust like one of the boys.


An important point to think about: When will you wear your Rolex? Is it going to be that nice formal watch you wear to weddings and job interviews? Or do you want a rugged piece you can take travelling, diving or hiking? If you’re never going to go deep-sea diving, a helium escape valve and waterproof case up to 3,900m are nice to have but non-essential. Are you a frequent flyer? Then get a second time zone with the GMT-Master II (below). If you want a reliable everyday watch, the Explorer is very decent. Narrow down your watch functions to what you’ll actually need so you can get the best use out of your timepiece.

Ex Managing Editor

Like most people these days, Melissa tells the time with her phone. She considers serious timepieces works of art and thinks the perpetual calendar is the handiest complication to date (pun not intended). She's also a Grammar Nazi but promises not to judge if you can't tell the difference between "guilloche" and "guillotine".