Another challenge accepted, and this time, it’s a hard one. As you know, €5,000 is not the Rolex-bag-filling stash it once was. Yes, I’m old, but it wasn’t that long ago that €5K was big money. Finding the best watches under €5,000 is not easy these days.

I say that reasonably subjectively, even understanding Lex’s point about expecting big-brand luxury for the money. And for some reason, some brands have deliberately nudged their prices just above the €5K cutoff to €5,100 or even €5,050. I’ve worked in sales for many years, so I’m pretty sure we all know the allure of €4,900 or €3,990, right? This simple psychology seems lost today, but I still found plenty of choices, albeit at oddly non-round figures.

The Best Watches Under €5000

Christopher Ward C1 Bel Canto “The Red One”

With a highly deserved GPHG Petite Aiguille prize from 2023, the C1 Bel Canto represents massive value to me. As far as I know, it is still the most affordable open-worked watch with a “Sonnerie au Passage” complication. And now Christopher Ward has collaborated with YouTuber Andrew Morgan on the design of “The Red One,” stirring my emotions. This version’s intense red sunray dial evokes luscious associations.

The Best Watches Under €5000

The brush pattern radiates out from what acts as a dial at 12. This appears as a hovering chapter ring, with the two hands affixed to a central bridge. The fact that the mechanics of the chiming complication are visible on the dial side is alluring. More than 60 new components form this module, which integrates with a Sellita SW200-1 base movement. It’s housed in a 41mm Grade 5 titanium case, and with such a striking design, this is a true value proposition for less than €5K. “The Red One” is available for pre-order until July 3rd. You can get it on a cheekily too-sporty three-row bracelet for €4,545 or a white rubber or gray leather strap for €4,095.

The Best Watches Under €5000

Orient Star M34 F8 Skeleton

Slim, in-house, and with a skeletonized hand-wound movement — where’s the catch? The only one is the image of Orient as a producer of value-driven watches like the sub-€500 Mako and Bambino. The M34 F8 is the brand’s halo model, and people are not conditioned to seeing a €3K+ Orient watch. For me, though, this is part of its allure, and for the price, I challenge you to find a skeletonized in-house-produced watch of this caliber (no pun intended, for once). Orient Star is Orient’s Grand Seiko, you could say, and it shows in meticulous detail. What’ll hit you first is the superb comfort of the 39mm case.

The Best Watches Under €5000

The case back is flush and combined with gently curved lugs with a 46.5mm stretch to hug the wrist. The case is only 10.8mm thick with the crystal, so we’re talking thin here, making the most of a missing rotor in the F8B6 movement. Rear Côtes de Geneve-like stripes vie with beveling and gray bridges for your attention, and the caliber shows generous perlage on the front. The finishing is primarily done by machines but exquisitely so. With a few choice blue details in the hands, it makes a proper impact. You’ll recognize the power reserve indicator at 12, an Orient Star standard, here offering a 70-hour readout under the applied “XII” numerals, another M-series trait. The M34 F8 Skeleton is available for £2,759.99 (roughly €3,266) from Orient Watch and selected dealers.

The Best Watches Under €5000

IWC Pilot’s Watch Automatic 36

At the moment, I haven’t got a quintessential pilot’s watch in my stash, and I’d sure like one. And while €3,000–4,000 used to be the tipping point, now even €5K is not that much anymore (well, it still is to me but not to the big brands). This little jewel remains relatively accessible, though. For some reason, judging from the brand’s promotional images, it is still heavily aimed at a female audience. Listen, IWC: small is the new big for many male collectors, including me.

The polished top section with brushed sides works exceptionally well with the deep blue dial, but it’s not a tool watch. If IWC made this 36mm version with an all-brushed case and the same dial, its sales would multiply. Mark my words, Mr. Grainger-Herr. But for now, at €5,000, I would happily put it on my list. But why does the black-dial version add a whopping €1,000 extra to get the multi-link bracelet? It’s a mystery, but I’d rather have the lovely blue alligator strap anyway. Check this one out on the IWC homepage.

Oris Divers Sixty-Five Calibre 400 38mm green dial

Oris Divers Sixty-Five Calibre 400

The Oris Divers Sixty-Five has been on my radar for years, especially the 40mm and smaller versions. I briefly had a 42mm one but sold it due to its size, and I keep wanting one despite my waning desire for retro. This year, green is hot, which is good for me as I don’t follow trends but love the color with a vengeance.

This is one killer combo in the neat 38mm case with the impressive Oris Calibre 400 inside. To my eyes, there is a newfound purity to the metal relief bezel, allowing the deep color of the sunray dial to shine. Plus, Calibre 400 offers antimagnetism, a 10-year warranty, and 10-year recommended service intervals. That’s pretty cool, especially if you, like me, enjoy the Divers Sixty-Five’s riveted bracelet with its sleek thickness and tapering design. For €3,600, this is a deep green win/win situation, and it’s on my list and maybe yours already too. Check it out on the Oris homepage.

Grand Seiko SBGW287

When searching for watches under €5,000, you’ll likely stumble across the gorgeous Grand Seiko SBGW series of 37.3mm models. Granted, at retail, they cost €5,100, but as Lex has rightly pointed out, you can tweak the budget or find a pre-owned example for less. It’s worth it. I might be incredibly biased here as I own the SBGW283, but how about the SBGW287? Just like my 283, this watch houses the beautifully finished 9S65 hand-wound movement. Visible through the sapphire crystal on the back, it can beat a €10,000 Swiss caliber in many respects.

By today’s slim standards, it’s not the thinnest, but does it matter? The winding action is silky smooth, verging on meditative therapy, but the 9S65 makes the watch quite chubby at 11.7mm thick. However, with the infinitesimal standards of the Zaratsu case finishing, every part of the case is silky smooth. Not to mention, the delights of the richly textured, deep red dial will make you forgive anything with each twinkle of its hand-polished indices. The SBGW287 costs €5,100 from Grand Seiko.

How do you feel about my selection, Fratelli? Would you need big-brand reassurance for your hard-earned €5K, or do you feel adventurous? Let me know in the comments if you agree with my subjective choices for the best watches under €5,000.