When I was in the market for my first Rolex, I was looking to spend around €5,000. At that time (about three years ago) that was enough money to buy an all-time classic Rolex model. You could easily get an Oyster Perpetual, Datejust, or Explorer for that money. The secondhand watch market has been stabilizing a bit over the past year, but still, I had to stretch the budget to €7,000 to get to those same references now. However, it’s nice to see that you can still get a very nice Rolex for well under €10K.

That’s especially comforting after having read Jorg’s article on the top five Rolex watches that you can currently buy under retail. The two-tone Explorer was the most “affordable” one on there, and if you have to pay import taxes, it’ll cost well over €10K. Not to mention, the other four were significantly more money than I currently feel comfortable spending on a watch. Let’s return to Earth for a moment and take a look at what you could get as your first Rolex.

Allow me to start with a short disclaimer: I am by no means a Rolex expert, let alone for pre-owned Rolex watches. I have simply searched on Chrono24 as if I were looking for my first Rolex too. Also, I am not affiliated with any of the dealers whose offerings I will highlight below. All right, with that out of the way, let’s get started!

first Rolex Oyster Perpetaul 116000

Image: House of Magic Treasures

Rolex OP, Datejust, or Explorer

If I were you, I’d always go for one of the 36mm classics like the Oyster Perpetual, Datejust, or Explorer. They’re classics for a reason, and with all of the different configurations for the OP and Datejust, you can still pick a personal favorite. I’ll start with a funky OP because that’s the one I clicked on first during my search. It is by no means perfect, which is weird for a Rolex. In that sense, it reminds me a bit of the current and former Rolex Air-King. But just as with that model, there’s something about it that I find rather attractive.

first Rolex Oyster Perpetual 116000

Image: House of Magic Treasures

This reference 116000 is from 2009, and it comes in the classic 36mm Rolex Oyster case. Currently, it is on offer for €5,695 with no box or papers. It has a glossy black dial with a circular guilloché pattern in the center, Rolex’s signature line of text around it, and then those funky numerals. The grooved centerpiece almost looks like an old record. The numerals at 3, 6, and 9 o’clock are very Explorer-like, but the weird thing is that they don’t follow the orientation of the other numerals on the dial. You could always go for a more classic-looking OP, but this one will certainly make some heads turn at your first get-together.

My old Rolex Datejust on its Jubilee

Rolex Datejust

My first Rolex was a Datejust. It was a reference 1603 from 1974 with a blue pie-pan dial, beautiful yellowed lume, and a jingly-jangly Jubilee bracelet. Unfortunately, it wasn’t love at first sight, and I quickly sold it and got myself a Cartier Santos instead, a decision I have never regretted one bit. But the lesson I learned from that experience is that I think I should’ve bought myself a more modern Rolex. The 1603 just felt too fragile to me. With its very loose links and Plexiglass crystal, it simply wasn’t a watch that I could bring anywhere, especially not near the water.

Image: Watch Deals

If I had to do it all over again, I think I would go for a neo-vintage Datejust like this 16234 from 1994. This watch is on offer right now for €6,950 with its box and papers. It has the classic blue sunburst dial and the ever-charming fluted white gold bezel. Indeed, the Jubilee bracelet from this era might not even be that much sturdier than the one on my ex-Datejust. But I think if you’d like a more solid bracelet, you’ll have to look at newer references, and then prices quickly start to climb toward the current list price of €8,950. To me, a blue-dialed Datejust simply is the Datejust to have.

my Rolex Explorer 114270

Rolex Explorer

Did you honestly think that I was going to leave this one out? It’s been almost a year since I got my Rolex Explorer 114270, and I still do not regret buying it in the slightest. It was on my wrist all summer long. It’s a watch that’s “there” when you need it but also “not there” when you don’t want it to be in your way. It looks perfect on its fully brushed Oyster bracelet and combined with the sloped, polished bezel. I don’t think I’d change anything about this watch. I even prefer it over the current reference — you can read why here.

your first Rolex Explorer 114270

Image: Timeless Vintage Watches

There are many 36mm Explorers for sale out there. As I said, I prefer the 114270 with solid end links. But there’s also the older and slightly cheaper 14270. In the 2010s, there was also a 39mm version, and Rolex currently offers the Explorer in 36mm and 40mm sizes. Those new ones will set you back €7,250, which isn’t that much more than the 114270 costs on the secondary market. But you’ll have to accept the inevitable waiting time before you can actually buy one. This 114270 from 2007 is for sale for the same price as the Datejust above — €6,950 with its box and papers — and comes with an engraved rehaut.

Image: Juwelier Burger

Bonus pick

All right, there you have it — my classic picks for the “my first Rolex” category. But what if you want to stand out a little more from the Rolex crowd? Well, then I can advise you to look at an Oysterquartz Datejust with an integrated bracelet. The prices of these may have increased even more than those of the classics mentioned above. But when I look at this Buckley-dial example that’s for sale for €6,450, my heart starts beating a little faster!

What do you think of the suggestions above? Do you have any others? Let me know in the comments below!