One of the best pieces of advice for finding deals is to look where others are not. Many people want vintage watches from the glory days of the 1950s and 1960s, or want the latest and greatest from the last few years. That middle ground is often forgotten because there’s not a lot of romance around it and because a lot of the watches are regrettable. But that just means better bargains for the good stuff.
It’s Chrono24’s 20th anniversary this year, and we’re looking back at the best neo-vintage watches from the 2000s(-ish). The Y2K era of the late 90s and early 2000s is not the first choice for many watch hunters, and that’s why we’re looking there today.
20 Years Makes a Difference
We’ve scoured the marketplace and rounded up our top-10 watches from this period, armed with everything we know today. These watches are horologically significant, have a decent investment value, or are just plain beautiful. You will find Rolex, plenty of non-Rolex watches, and one (well, two) that I shouldn’t say more about because I’m currently saving up for them. But why don’t you see for yourself?
- Audemars Piguet Royal Oak 25594
- Rolex Daytona “Beach” 116519
- Rolex “Zenith” Daytona 16520
- Zenith Rainbow Flyback El Primero 02.0480.405
- TAG Heuer CS3110 and CS3110
- Cartier Santos 2319
- Rolex Turn-O-Graph 116264
- IWC Da Vinci Perpetual Calendar Chronograph 3751
- Omega Speedmaster 3594.50
- Patek Philippe Aquanaut 5060A and 5060J
1. Audemars Piguet Royal Oak 25594
Let’s start off with a 36-mm Royal Oak from Audemars Piguet. It’s the ref. 25594, and it comes in a range of case materials and dial colors. Because of the integrated bracelet, the watch wears closer to 38 mm than 36 mm. The dial layout is just beautiful, with the symmetry of the day and date subdials and the moon phase that really pops as it catches the light. This is a very wearable model that offers more horological firepower than a standard time and date Royal Oak. Prices are slowly and steadily trending upward, so you’ll avoid the volatility of the more mainstream Royal Oak references and won’t lose money on the sale either.
2. Rolex Daytona “Beach” 116519
If you like the colorful rarity of Rolex Stella dials, then you should definitely take a look at their peers from the Daytona lineup. We’re talking about the Rolex Daytona “Beach,” a quartet of absolutely out-there Daytonas in pink mother of pearl, yellow mother of pearl, green hardstone, and blue lacquer. Each is housed in a white gold case with a rare Roman numeral Daytona dial.
These watches have been popping up more and more at auctions, and they’re certainly hard to forget. The straps alone are enough to make you fall in love, and they’re a definite departure from the often sober and methodical Rolex way of doing things. Price-wise, pink is generally the cheapest and starts around $50,000. Yellow is a little more expensive than green, and the blue is on top at around $150,000. They’re not cheap, but they’re a beauty to look at… and looking doesn’t cost a dime.
3. Rolex “Zenith” Daytona 16520
Before Rolex created their own in-house automatic chronograph caliber, they had to use one from a third party. And why not choose the (arguably) first automatic chronograph movement, one that’s changed very little over the last 50 years? We’re talking about the Zenith El Primero movement inside the “Zenith” Daytona ref. 16520.
You’d think the next generation with Rolex’s first in-house automatic chronograph caliber would be a collector’s darling, but instead it’s the 16520 Zenith Daytona that’s sought after. Why is that? Well, the watch world loves an oddity, and this is an unusual piece of history for Rolex and the Daytona. Prices for these watches seem to have stabilized at around $35,000 for the white dial and around $40,000 for the black dial.
4. Zenith Rainbow Flyback El Primero 02.0480.405
Speaking of Zenith, there are deals to be had on the Zenith Rainbow Flyback El Primero. This model was developed for the French Air Force in the mid-1990s, and the agreement was that Zenith would deliver 1,000 watches annually over a four-year period. But here’s the thing – shortly thereafter, an election happened in France and the contract was canceled, leading Zenith to pivot and present the watch as a civilian model at Baselworld 1997.
It’s 40 mm wide, 12.6 mm thick, and features the El Primero Caliber 405. Colorful watches are having a much-deserved movement, and why not maximize this with the Rainbow Flyback El Primero? Oh, and prices start around only $3,500.
5. TAG Heuer CS3110 and CS3111
Let’s stick with the theme of affordable chronographs and talk about this killer Carrera from 1994. We’ve got the CS3111 in black and the CS3110 in silver. These were released on the 30th anniversary of the Carrera, and they’re one of the best-kept secrets in neo-vintage chronographs.
This watch was created after TAG had taken over Heuer, but the DNA here is all vintage Carrera. The case architecture is super sharp with those long, elegant lugs. You have tritium on the hands and hour markers, so it only gets better with age. And it’s 36 mm in diameter, so if you have a small-to-medium-sized wrist and want a chronograph that you can comfortably wear, then this is a winner. It’s also rather affordable, with starting prices around $3,000.
6. Cartier Santos 2319
Ok, here’s one that I should probably keep a secret because I’m saving up for it myself. It’s the Cartier Santos ref. 2319 made for the SIHH watch fair in 2002 with a production run of 2,000 pieces.
The watch has much of that classic Cartier look and feel but with the added sportiness of the luminescent hands and hour markers atop a slate gray dial. Think of this as Cartier’s version of the Rolex Explorer. It comes in a 29-mm case, but because of the square shape, it actually wears closer to 35 or 36 mm. This watch would be an ideal candidate for a comeback edition, but you can still find the neo-vintage versions floating around at about $7,500, and they’re only getting more expensive.
7. Rolex Turn-O-Graph 116264
This is our last Rolex for today. People get tired of hearing about them, but this watch is cool. It’s the Rolex Turn-O-Graph, sometimes called the “Thunderbird” because of its connection to the US Air Force aerobatics team. It’s a spin-off of the Datejust, and its rotating bezel served as the blueprint for the Submariner, so it can be considered the godfather of Rolex sports models.
You can find four-digit references from the 1950s, but today we’ll focus on the final examples from the early 2000s. They sport the classic 36-mm case in either steel or two-tone. You’ll also get a roulette date wheel and that striking red second hand.
If you’re looking for a go-anywhere, do-anything watch somewhere between sport and dress, consider this one. It’s unlikely to be reintroduced, which only adds to the rarity of these pieces. Prices for the 116264 start around $6,500, so they’re fairly affordable and fairly stable in price as well.
8. IWC Da Vinci Perpetual Calendar Chronograph 3751
Next up is a solid gold perpetual calendar split-seconds chronograph starting around $12,000. I’ll repeat that, a solid gold perpetual calendar split-seconds chronograph for the price of a Datejust 41.
For some excellent neo-vintage, check out the Da Vinci. This IWC ref. 3751 debuted in 1995. You have IWC’s signature perpetual calendar display, with the four-digit year window down near seven o’clock. That’s combined with a rattrapante i.e., split-seconds chronograph module for timing multiple events. And that’s all wrapped in 18-karat gold or platinum if you like.
The Da Vinci’s floating case is an acquired taste if we’re being honest, but the value for money is undeniable.
9. Omega Speedmaster 3594.50
This is the other watch that I’m currently saving up for, so maybe just skip this part of the article… It’s the Omega Speedmaster 3594.50 which is unfortunately named the “Replica.” The watch debuted in 1997 to commemorate the 40th anniversary of the Speedmaster and had a six-year production run, ending in 2003.
Some may call it the Frankenwatch, but it feels more like a greatest hits collection. It pairs the original broad arrow style handset with a later MoonSwatch style case with the lyre lugs. The steel bezel is a beautiful touch, as is the applied Omega logo and the retro typeface for the Omega name. It’s got the caliber 1861 inside, so it’s easy to maintain and repair when you must.
Prices can go as low as $4,000, but you’ll want to watch out for signs of corrosion on the hands and perhaps pay closer to $5,000 for a worry-free example.
10. Patek Philippe Aquanaut 5060A and 5060J
The Patek Philippe Aquanaut ref. 5060 was launched in 1997 to help attract younger customers to the brand. They should’ve just invented Instagram, but this works too.
The Aquanaut has seen a huge rise in popularity in the last few years, but why not snatch up the original? You have your choice of sporty steel and dressy yellow-gold, both starting around $38,000. The watch was originally unveiled as the “Nautilus-Aquanaut,” and you can still find examples with the word Nautilus printed on the clasp.
The Y2K era of the late 90s and early 2000s is a goldmine if you know what to look for, and this top-10 list is enough to get you started down a few rabbit holes. And remember, sometimes it is worth looking where other people do not.
Want to read more about our best-selling watches? Then do not miss Pascal’s article on the most popular watches on Chrono24.
