Staff Picks How We'd Spend $20,000 On One Watch

The resulting picks cover a wide range of tastes, from dressy and old school to modern designs, independent brands, and more. Take a look below and then let us know in the comments what you would pick if you were given the same budget. 

This isn't the first time I've written about this particular A. Lange & Söhne Saxonia. I previously showcased the watch as part of our Entry-Level series in which this watch was – as of May 2022 – the least expensive timepiece for sale from the brand. At 35mm in either pink or white gold (pink is my preference) and a silver dial with an elegantly designed time-only, small-seconds layout, this particular Saxonia is pure archetypal understated horology. It's a watch that, at the time I last wrote about it, retailed for $19,700. These days Lange doesn't list the price for the watch publicly, so while it may have barely eclipsed the $20k parameters of this exercise in 2023, I don't care. It's harder than you think to find a watch at this exact price point.

When it came time to answer this $20,000 question, though, my mind immediately wandered back to this Lange. And while I am currently not in the market for a new five-figure timepiece beginning with the number two, I have a feeling this Saxonia will take up valuable real estate in the old noggin for the foreseeable future. There's just something about a 35mm watch with a 25mm-large, hand-wound movement inside that has been decorated to Lange standards. Don't be shocked to see me wearing one someday.

–Danny Milton, Managing Editor 

I'll start this by saying that I know I'm cheating here. This watch was released in 2022 for the 10th anniversary of the Octo Finissimo in only 200 pieces, and it's long since sold out. But since it cost around $19,300 at release and someone has one listed online for less than $20,000 (most other people are asking more), I'm going for it. 

I've long been fascinated by, and in love with, the Octo Finissimo Chronograph GMT thanks to its incredible design, wearability, and technical achievements (the thinnest chronograph ever made and just so happens to be automatic and a GMT). But there's something about the "Sketch" that just seems perfect.

I grew up around artwork and artists, and even though I don't have any real ability to draw or sketch a design, the dial reminds me of watching near and dear artists form something incredible from nothing but their minds and a few art supplies. The fact that the dial came from the first designs of Bulgari's head watch designer Fabrizio Buonamassa Stigliani adds a perfect layer of story to an already great watch. Maybe I'll own a non-sketch Chronograph GMT someday, but it might be hard to stomach knowing this watch is the one I really wanted all along.

–Mark Kauzlarich, Editor

I am acutely fixated on Serpentis, and vintage Tubogas watches these days. Scroll for Serpentis endlessly by day, dream of Serpentis feverishly by night-levels of obsession. I tried desperately to use my $20k on something more "watchy" but stopped myself and accepted my truth.

This is the ultimate jewelry and watch crossover piece. If I had more than $20k, I would start exploring Tubogas with JLC movements, but one must stick to the rules. So I'm going with early 2000s yellow gold, round case, black dial, Tubogas. I will wear her all summer long and suffer unsightly tan lines in the name of looking good.

–Malaika Crawford, Style Editor

Twenty grand is a good chunk of change. For that kind of cash, I want something substantial, something timeless, something gold. But also something I can wear every day. So I landed on a Rolex Day-Date ref. 18239 in white gold. This is the Day-Date that Rolex introduced in 1988 and produced through the early 2000s. Sure, the vintage purist in me wanted to go for an even older 1803, but I decided on the more recent reference for a few reasons. 

First, this is when Rolex introduced a double quick-set caliber, meaning both the date and day can be changed with a quick turn of the crown. Second, those old examples get worn down, and the bracelets get stretchy. If I'm wearing a Day-Date, arguably the most luxurious of luxury watches on the planet, I want to feel lavish, damn it. I want solid bracelet links, a sapphire crystal, and a date I can easily change in a few seconds.

Just in the past week, I've seen a couple of examples on bracelets in great condition listed for around 20 grand (here and here). I chose white gold first of all because they're a touch more expensive than yellow gold and why wouldn't I stretch every penny out of my budget? But also, for $20,000, I want something I can wear every day. I'm a little too self-effacing to wear a yellow gold Day-Date all the time, but a white gold one might be just sneaky enough that I could make it work.

And when the modern version of a Day-Date 36 costs about twice as much as this, I might even say the 18239 is something of a value proposition.

–Tony Traina, Editor

Yes, in real life, and particularly in my real life, Tony is right. $20,000 is a lot of money. But, in the land of picking watches for "content," my initial reaction was, "well, that's not enough." Luckily, I found something worth my while after consulting the various watch lists I maintain for an "if I ever hit the lottery" kind of rainy day. I love a 1990s Patek. It's a bit classic and a bit ugly or odd in the way that only this decade can deliver.

The ref. 5000 leans towards the classic end of that spectrum whereas the ref. 5085 Neptune hits the other. The resulting watch is dressy enough, sporty enough, and just off the beaten track enough for me to wear most days. Flip the 5000 over, and we find an exhibition caseback showing off the caliber 240 PS. This is the same base caliber as the ref. 3940, heard of it? Beyond a nice view of Patek's excellent finishing, I love how the movement fits this smaller case, more like it was made for this sizing as opposed to how it fits the up-sized big brother ref. 6006.

I'm taking the white gold variant of this 33.5mm Calatrava which can still be had right at our $20k number, luckily. At this price point, I'm looking for wearability and a bit of wow factor in a design that hits the right notes for me. From the sizing to the dial design, this "dated" Patek has all that and more.

–Rich Fordon, Client Advisor, H Shop

If you're forcing me to spend $20,000 of my own imaginary, hard-earned dough, I'd have a difficult time spending it all on anything traditional or normal. A classic watch design is cool and all, but my brain would be telling me, "Live a little, man. You're rich now!" Some people are into heritage or case material, or maybe even complications, but I really get a kick out of fun designs, which is why I'd go with the Trilobe Une Folle Journée in the Dune colorway.

It might sound like a weird choice for some, but I've been on a little independents kick lately, and Trilobe's orb-like watches with their unique ring system for time-telling are like nothing I've ever seen before. Sure, I'd be scared of hitting that massively domed sapphire glass onto something, but again, I'm trying to live my best life here. Even with that bulbous crystal, the watch is surprisingly wearable because the case itself is only 40.5mm in diameter and 10mm thick. I can see myself admiring the watch quite a bit and enjoying the fact that I have something unique on my wrist that I won't see other people rocking on the streets of Los Angeles.

My only problem is someone is going to have to lend me a few more Hodinkee bucks because the Une Folle Journée is a little over budget at $21,700. Oh, well. You only live once. 

–Brandon Menancio, Editor

Working in the watch industry comes with it the Privilege of Proximity, and therefore the ability to see and handle many watches that otherwise I'd never have the ability to share the same room with, let alone live out my rollercoaster tycoon fantasy and actually get my hands on these things. I've been in this business a while, long enough that finding something "special" (to me) becomes ever more difficult. When you see watches all the time (day, night, dreams, AND nightmares), they've got toreally mean something, you know?

That being said, my imaginary $20k needs to be spent wisely, if all in the same place.

Enter the Breguet Tradition. At the time, having just started working in the watch world, this was the first watch I came across that showed me what a high-end watch could be. Everything I had experienced at that point was part of the usual suspects: Rolex, Omega, Breitling – all nice watches, but all pretty much what you'd expect: small clocks. The Tradition is also a small clock, but a small clock with all the magic parts made visible – on the front. And not only visible but symmetrical! It was (and still is) so cool! I remember where I was standing, what the carpet looked like, the window I was standing next to, and even that it was a nice sunny day outside. It made a huge impression on me, a moment of true wonder.

If you ask me now, and you are asking me now, I'd tell you I've learned a lot in those years since I first saw a Breguet Tradition. My tastes have changed remarkably (poor guy had no idea – bless his heart), and I've come to better appreciate other perspectives. What I have learned most of all about my own relationship with these things; is that watches, for me, act as tokens of a time and place. My dad's watch taught me that.

Practically speaking, a watch in my collection needs to fit into a specific role (of which I have identified four: Every day, Dress, Vintage, Something-Inside-Baseball). Watches with overlapping duties are okay, but I can't have any duplicates, such as two Vintage options. Otherwise, there will be pieces that go unworn. The Breguet Tradition hits all the right notes for me as something with lots of heritage and watchmaking chops, and most importantly reminds me that even after it all, watches can still be, in the truest sense, wonderful.

–Jonathan McWhorter, Video Producer

If I'm about to spend $20,000, I want a watch that is decidedly out of my usual zone. So no dive watches or even, more broadly, sports watches. I also feel as though a $20,000 watch should be gold and, preferably, complicated. 

Bearing all that in mind, I think I'd start hunting for an Audemars Piguet 25548 Perpetual Calendar. Initially launched in 1978 as the 5548, this round-cased QP uses the same movement found in the early Royal Oak QPs (a fav of mine, but well over today's budget) and does so with a 36mm footprint and a lovely white dial.  

As much as the Royal Oak is AP's signature creation, I tend to think of AP for its complications, specifically the brand's very early work with perpetual calendars and the glorious reference 5516s. As such, a 25548 is an excellent highlight for the non-Royal Oak side of AP. In yellow gold, they can be found for just under $20,000, and, despite my generally toolish watch proclivities, an AP QP would be an absolute grail purchase for me. How wonderfully decadent.

–James Stacey, Lead Editor