Best Watches to Buy If You Have $5000 to Burn

Well, the returns have been good, and you’re considering maybe upgrading to an expensive car next year. So what if the car payment doubles or triples? And yet, your watch is still only worth $300. At the risk of accidentally snapping a photo of a Benz logo with an entry-level Citizen, how would you match your steering wheel to your watch strap, your vehicle to your timepiece?

A good problem to have, to be sure. When is the right time to buy a $5000 watch? Maybe you have a few properties, a car, steady cashflow, and you’re thinking about upgrading something. $5k isn’t enough for a downpayment on anything major, so at this point it might be one month of cashflow that is tied up in wrist equity. And while I’m certain there are even financing options for such a watch, I will give you my top recommendations if I was in your shoes, and leave it to you iron out the finances.

Entry-Level Luxury

So $5000 is the new entry-level luxury. It could be considered the top end of that category, which starts at $2500-$5000. The next tier would be non-prefixed luxury, at $5000-$10,000. And anything beyond that is perhaps in the realm of ultra-luxury, which is an art world extravaganza of its own, where numbers are made up.

The benefit of a $5000 watch over other price points is that it is in a sweet spot. It’s high quality enough that you can buy just one and keep it for a lifetime. It’s good enough to pass on as a treasured heirloom. Anything cheaper, and you may always be stuck with the thought of “what about the much nicer watch for just a little more?” You don’t have that problem in this price range. For more money, your returns are increasingly marginal (even perhaps negative return on quality per dollar if you manage to pay for a Rolex – though not factoring in inflation and resale value).

Another aspect is that in this price range, you are dealing strictly with Certified Chronometers. Who can be bothered with the pleasantry of resyncing your watch once a week because it gained or lost 5 minutes? With a Chronometer-grade movement, you will only lose that same 5 seconds once or twice a month. These are not atomic watches, after all; I am only looking at mechanical timepieces today.

You get the picture. Let’s begin.


First, let’s look at Omega. This is a Swiss brand that has innovative technology to make accurate chronometers of the highest caliber. In the last decade, Daniel Craig’s James Bond has worn one or two models per movie, even scoffing at Rolex (which his predecessors sometimes wore) on screen in Casino Royale. This is the same guy who drives an Aston Martin, but also a Jaguar and sometimes a Toyota – a man of diverse price ranges, but always fashionable or utilitarian.

As you may know, in addition to being funded by British intelligence as government propaganda, the 007 series is also a cash cow for major advertisers like Heineken, Rolex, Omega, Seiko, Aston Martin, Jaguar, and even Toyota. Because why not? As a result, it’s safe to emulate Bond’s materialistic appetites and be looked upon favorably by a judicious public, and thus borrow an essence of the dancing commander with a cool $5k check. But I digress.

With Omega, you have 3 choices: the Speedmaster, the Seamaster, and everything else. Let’s begin with the Seamaster because Bond wears no Speedmaster. If there was any point to the previous paragraph, it’s this: Omega watches come pre-packaged with a mythos. Whether it’s the legacy of a movie hero, or a real-life astronaut, Omega has a long and deep history few other brands have.

Omega Seamaster

First, it’s a really cool name, let’s be real. The Omega Seamaster line is the water-sports line of the brand. In this collection, you will find four main models:

Image credit: Omega

Aqua Terra

Image credit: Omega

The Aqua Terra is one of the more interesting Omega watches. It’s more subtle (in a good way) than some of the other dive watches, and blends a sporty aesthetic with a utilitarian design, and a distinct fashion statement. The hands and indices are sharp and pointed, like a piercing arrow of the sun. The sun part is from the reflective dial, which is accentuated by horizontal striping, for a sunset and sunrise in every reflective angle.

As you can see, there’s an endless number of variations on these watches. Personally with any watch in this price range I would go for a bracelet version where possible, and find alternate strap options aftermarket. You can’t get a good aftermarket bracelet, on the other hand.

At 150m of water resistance, the Aqua Terra cannot seriously be considered a “dive watch.” This can come at the detriment of the watch fanatic who might insist that 200m is the minimum rating for a dip in the pool. I might insist the same, but the watches in this price range take their depth rating more seriously than a cheap one – you’re good for a solid 300ft, but I still would not take it full-blown scuba diving. Perhaps merely lounging with a swim from a sunny boat.

These watches come in both 41mm and 38mm. Personally I find the smaller size is perfect for casual everyday wear, and the larger is more of a commitment to have metal on your arm. Their thickness is 13.8mm and 13.2mm, respectively. Personally I like my watch thickness under 12mm where possible, so I would really have to like it when I saw it in person to sway me for these “slightly thicker” options. Of course, I am complaining about 1-2mm; luckily for you, you probably won’t notice until a few months into wearing it.

They have some ultra-light titanium options in the Golf series that look awesome, but they start to double in price for that.

The Omega Seamaster 300

Image credit: Omega

These are all 42mm watches with a 300m depth rating. This is considered the quintessential Seamaster of the 2000-present era. It’s got that helium escape valve at the 10 o’clock position in case you really do go saturation diving. By the way, that’s the one where you need a week or two in a decompression chamber, because 1000ft is quite deep. So maybe it’s a little overkill on the pressure rating, but remember that if you bang a 200m-rated watch against a rock at a 100m depth, it will be much more fragile than a 300m watch. It’s just an added layer of robustness, at the end of the day.

These watches all come in some really cool special editions, and as you can see, they will have a multitude of color and strap options. Personally for me, for everyday wear, this watch is too big at 42mm and a 13.5mm thickness and 191g in weight.

Planet Ocean

Image credit: Omega

Well, the Planet Ocean watches are bigger, bulkier, more expensive, and have 600m water resistance. They look really cool, but they are both outside our price range and too big for my tastes. I would not recommend them as I personally would not get one, but you should check them out in person and see how you feel.

Design-wise I think they are on par with the Aqua Terra and make the Seamaster 300 look ugly by comparison.

Image credit: Omega

They do also come in a 39.5mm version, but those have a thickness of 14.5mm – that’s a big commitment for me.

Seamaster Heritage and other models

The heritage section includes Seamaster models from decades past that have been revived and re-released with updated production and technology. This is worth perusing, but they do all have a vintage flavor that you may not be ready for. I will just post some examples of watches from the collection that I like, as well as others that are simply out of production:

Image credit: Omega
Image credit: Omega
Image Credit: Hagerwatches

Omega Speedmaster

Image credit: Omega

Just to cover it briefly – the Omega Speedmaster was a premier chronograph back in the day, and was later adapted and developed for NASA to their specifications along with a handful of other brands. The Omega Speedmaster has the honor of being the first watch on the moon, worn by both Lance Armstrong and Buzz Aldrin, who to this day wears three at a time on his wrist(s).

Image Credit: Hodinkee

Here’s what you’re dealing with:

Image Credit: Amin Reviews

It seems like every year, Omega releases a limited edition of these watches, some of which are astounding:

Image credit: Omega

Do some homework on which Speedmaster you’d like. For the price, I like the classic Speedmaster Professional. One caveat here is to make sure what kind of crystal you are getting. Sapphire crystal is the gold standard in modern watches, which will essentially never get scratched. However, primarily for a “vintage aesthetic,” the cheaper Speedmaster versions use a much softer Hesality or acryclic crystal. These are less prone to shattering, but much more prone to acquiring scratches. From a utilitarian perspective, Hesalite was preferred in space operations, but that is changing.

Image Credit: Hodinkee

To get an interesting look into what modern atronauts wear in space, check out their “Instruments” page, which has rather uglier watches but that are designed to modern astronaut specs.


Tudor is the new Rolex – that’s what you need to know. Imagine if you took two Rolexes. One of them you triple the price tag and limit the supply. The other, you change the logo from Rolex to Tudor and keep the price the same. It’s the same watch with a new label, at the old price.

Both are made by the same company (Rolex aka the Hans Wildorff Foundation), and use the same materials. Compared to Omega, I believe that even Tudor watches are overpriced, but they do have some crisp designs that will still give you a sliver of “the feeling of wearing a Rolex,” which, I am told, is the real product.

Tudor Black Bay

Image Credit: Tudor

These watches can come in quite under budget, and come in a dozen colorways. The Black Bay is the Tudor classic dive watch, their version of the Rolex Submariner. Instead of a cathedral-type hour hand, these watches have a unique snowflake-shaped handset.

Image Credit: Tudor

These are 41mm by 13mm thick, which is comparable to those Omega watches from before. Personally I don’t find Tudor designs as interesting as Omega or Grand Seiko, by the way.

Tudor Pelagos

Image Credit: Tudor

The Tudor Pelagos has a more interesting design in my opinion, the main difference being that the indices are square to match the angular nature of the hands. They are bigger at 42mm x 14.3mm thick. The steel versions weigh in at a solid 157g, but the titanium ones are a cool 104g, so I would recommend those for the same price.

Tudor Black Bay 36

Image Credit: Tudor
Image Credit: Tudor

The Black Bay 36 is my favorite of the Tudor options. It’s a classic 36mm size, but also comes as 41mm. This is a big difference, and I think the 41mm loses the cool collected elegance of this original and is trying too hard to be noticed. I’ve seen others wearing this watch and it’s strikingly recognizable and flashy even so.

However, at half of our budget, this may be considered an entry-level luxury watch even more, maybe something you give to your son as a college graduation gift.

Grand Seiko

Whereas the other two were Swiss Made, Grand Seiko is made by Seiko – the oldest Japanese watchmaker in the world. This is their top-of-the line collection, showcasing expert Japanese craftsmanship and artistry – both in design and in technology.

If you’re looking at Grand Seiko, I would personally pay attention mainly to the Spring Drive collection. This is a movement technology that Seiko invented, which is a hybrid of a mechanical and battery operation, and produces a signature seconds-hand sweep of infinity ticks per second. That’s a bold claim, and for reference, any other watch besides a Spring Drive will have a classic mechanical sweep of 6 to 10 beats per second. But with a Grand Seiko, if you slow down the video, you will get no seconds’ jumping. You can stare and be mesmerized by a seemingly-impossible feat. Really you will just have to see it in action.

To observe this action, which incidentally features many of the watches in this list, I recommend taking a look here:

Besides a Spring Drive, the finishing on the watch case and surfaces is second-to none. Even Patek and Audemars, watches costing 10-100x more, don’t take such care in their finishing; even moreso, Rolex or Tudor finishing and quality seem barbaric by comparison (a testament to the power of marketing). Either that, or Grand Seiko is severely underpriced – although be aware: the market is starting to recognize it and all Seiko watches are moving upmarket and displacing “Swiss Luxury” with Japanese Mastery.

Grand Seiko has tons of options, I will just give a few examples:

Image Credit: Grand Seiko

These are classic designs that are well-thought out. The dial on this particular piece has a snowflake texture you have to see in person or dig into videos.

They just came out with a limited edition version of this watch, which is stunning:

Image Credit: Grand Seiko

There are also a plethora of sport GMTs, which is actually quite handy for tracking multiple time zones. If you travel abroad for business or pleasure, it’s good to have a secondary hour hand to keep track of your internal clock, after all:

Image Credit: Grand Seiko
Image Credit: Grand Seiko

And finally, for a classic example, here’s a dress watch:

Image Credit: Grand Seiko

As you can see, Grand Seiko isn’t trying to reinvent the wheel. They’ve found what works and are dedicated to making it into the highest form of artistic mechanical expression, with extremely tasteful experimentation in the forms of limited editions. While a playboy might wear a Rolex, maybe a budget playboy would wear a Tudor. A classy man might wear an Omega. But a connoisseur of the finest things in life, a man who respects mastery and the pursuit of excellence in all things would be found with a Grand Seiko

And that is why you don’t see it being worn very often. From a distance, it may be mistaken for a Seiko. Thus you have to ask yourself, why are you wearing a watch – for yourself, or to make others think certain thoughts and feel certain feelings? Because that can be accomplished with a $200 Rolex Yachtmaster repica.

Incidentally, if you like the aesthetic, then the Seiko company has a subsidiary called Orient, which has an upper tier collection called Orient Star:

This is a combination of a Grand Seiko and Aqua Terra, although not Spring Drive. Incidentally, I have this watch for sale for around $1000. It’s in the category of “Baby Grand Seiko”:

Other Options

Overall, these are the main watch brands I would recommend to someone looking to blow $5000 on a long-term watch. I would personally go with an Omega Speedmaster, followed by a Grand Seiko Spring Drive, followed by an Omega Aqua Terra.

There are some pricier luxury brands that do have some lower-end offerings in this price range, but their staples are more expensive. Here are some examples, you can find more info on by searching the brand name in Google images or clicking those image credit links:

Image Credit: IWC
Image Credit: Rolex
Image Credit: Zenith
Image Credit: Nomos


And there you have it, a respectable list for someone that has $5000 but no idea what to do with it. By the way, most of these watches have great resale value. In fact, for my friends I would recommend finding a reputable resale market. However, watch out for fakes and watches with swapped components by only dealing with certified sellers and verified merch – buy the seller, not the watch.

Also, keep in mind the age of the watch. If it is over 5 years old, you will have a servicing bill in the near future. I would allocate $500-$1000 for that cost, payable once a decade. So like a car approaching it’s first 100,000 miles, that is a good time to sell and buy the latest toy.

But who needs such headaches? The cure for such entanglements is to buy a new watch, put your own mark on it, and decid what to do with it after many years, after many adventures. Whatever you do, remember to have fun; otherwise – what’s the point?

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