Hidden Gems: Rolex Deals in Late October 2023

For the third installment of Hidden Gems – our biweekly series highlighting the best deals in used Rolex – I’ve decided to change things up and introduce categories. Instead of just highlighting sports watches around $10,000 (still where I see the most value in the current used Rolex market), we’ll take a look at three archetypes: the everyday watch, the purpose-driven watch, and the fun watch. You’ll still get your fix of true value propositions (e.g. a $7,000 Sea-Dweller 16600), but you’ll also see some out-there and purpose-driven picks that you may have otherwise missed. 

As I like to note in these types of articles, you should never buy a watch solely based on market trends. Any money spent on a wristwatch is money you should be fine with losing. Buy watches to wear them, love them, and pass them on. Without further ado, let’s look at three hidden gems in late October of 2023.

The Everyday Watch - Rolex GMT-Master II 16710

Image Source: lunaroyster.com

In our recent article The One-Rolex Watch Collection: Our Picks, I chose the Rolex GMT-Master II 16710 “Coke” as my hypothetical one-and-only watch. I see it as the perfect everyday pick; you get the quality and reliability of a fairly modern Rolex in a pared-down pre-Super-Case silhouette. With plenty of water resistance and a second (and optional third) timezone, the GMT-Master is a perfect daily companion. The 16710, known as the second GMT-Master II, had a very long production run (1989-2007). With that, there is plenty of variety within this reference number: lume material, solid/folded endlinks, caliber 3185, 3186, drilled lugs, dial variations, etc. You also have three bezel configurations to choose from: the infamous blue and red “Pepsi”, the black and red “Coke”, and the all-black variant. 

Image Source: analogshift.com

While researching the aforementioned article, I came across a few 16710 listings, most of which surprised me with their pricing. These watches hover around $10,000, of course depending on year, condition, and extras (box, papers, stickers). This is near-double their original retail price, even accounting for inflation, but in today’s GMT-Master II market, $10,000 feels reasonable. 

The Purpose-Driven Watch - Rolex Datejust (Any 5-Digit Reference)

Image Source: almawatches.com

In the watch world, “purpose-driven” is most often used to describe tool watches: dive watches, pilot’s watches, racing chronographs, etc. The Datejust usually doesn’t come to mind. However, there’s no doubt that the Datejust serves a very specific purpose. For decades, it’s been a symbol of elegance: the go-to luxury watch for generation after generation. Its fluted bezel and cyclops date window are recognizable even by non-enthusiasts. Simply, the Rolex Datejust is an icon.

Over its lifespan of 80 years and counting, the Datejust’s design hasn’t changed much, making older and vintage examples – that are often priced lower – very appealing value propositions. To me, any Datejust with a five-digit reference number is a good place to start. The five-digit generation introduced the quickset date function: a non-negotiable if you don’t plan to wear the watch every day.

Image Source: hqmilton.com

Five-digit Datejusts are split into two major categories: 160xx (1977-1988) and 162xx (1988-2005). The latter features a sapphire crystal instead of acrylic, 904L steel case instead of 316L, and a caliber 3135 instead of the 3035. It’s a technically superior watch, but if you’re deal hunting, the older models are worth a look. That said, these two generations are surprisingly similar in their pricing. Both can be had for less than $5,000, all day. If you’d like full gold, diamond indices, or a fun dial, you might break that threshold, but not by much.

It’s important to note that, especially with vintage watches, you need to do your homework: not just on the watch, but the seller. Always buy the seller. Ask about the watch’s service history, which components (if any) have been replaced or modified, and ask for additional pictures. If they don’t want to answer questions or send pictures, you don’t want to buy their watch. 

The Fun Watch - Rolex Daytona 116508 Green Dial “John Mayer”

Image Source: time4diamonds.com

No – this is not a bargain. I’m frankly not even sure it’s a good deal. However, this is the fun pick – you gotta live a little. The Rolex “John Mayer” Daytona 116508, following two exorbitant price peaks in Spring of 2022 and Spring of 2023, is at its lowest price in years. For those unaware, the once-overlooked green-dial Daytona was made wildly popular by John Mayer in his second episode of Hodinkee’s Talking Watches. He described it as a future classic, saying that we’ll all look back and wonder “why didn’t we know!?”. Of course, this led watch enthusiasts and non-enthusiasts alike to buy every example on the market and shoot up the price. At one point, these were selling for $150,000: more than 4x retail. I’m not saying that the green-dial 116508 is a steal now that it’s “only” double retail, but hey, this is the fun pick after all. There's no denying that this is a special watch. The Daytona is Rolex's most sought-after model, and the green and yellow gold configuration is quintessentially Rolex. I have no doubt in my mind that this watch will continue to be highly sought-after. If the green dial 116508 isn't a future classic, it's because it's already there.

These watches are listed in the neighborhood of $80,000, but I’m seeing completed auctions and sold examples closer to $75,000. Like I said, this watch is far from a value play (from what I can tell), but if you’ve been in the market for a John Mayer Daytona, and (understandably) have been scared off by 6-figure prices, it’s time to start looking.