Watch collecting is rarely a one-way street.
You buy something, love it for a few years and eventually another watch catches your attention. Selling one watch to fund the next is all part of the hobby.
But some watches are different.
Not necessarily because they’re the rarest or most expensive, but because they have the history, design and personality to keep pulling you back.
These are five I’d want to keep.
1. Omega Speedmaster Moonwatch Professional
The watch with a story nobody can recreate
Predictable?
Probably.
But there’s a reason the Speedmaster appears in so many collections.
Its connection with NASA and the Moon is genuine, its design has remained remarkably recognisable and, unlike plenty of watches with great stories, it’s still something you can comfortably wear every day.
But the thing I’d miss most is the ritual.
Taking a moment to manually wind a Speedmaster is part of owning one. In a world where almost everything is automatic, digital or permanently connected, there’s something wonderfully old-fashioned about it.
Would I eventually be tempted by another Speedmaster?
Almost certainly.
Would I sell the Moonwatch to fund it?
Probably not.
2. Rolex Submariner
Because sometimes the obvious choice is the right one
The Submariner might be one of the most predictable watches you can buy.
I don’t mean that negatively.
It’s predictable because Rolex got the formula so right that almost every dive watch made since has, in some way, had to exist in its shadow.
It’s tough, incredibly versatile and instantly recognisable without needing to be flashy. You can wear one with almost anything, which is exactly why I’d find it difficult to sell.
There will always be newer Rolex models.
There will always be watches with more unusual complications.
But sometimes you don’t need interesting.
You need the watch you know you’ll still want to put on in twenty years.
For me, the Submariner is one of those watches.
3. Cartier Santos
The one that makes the collection more interesting
We’ve talked recently about why Cartier seems to be attracting so much collector attention, and the Santos is a perfect example of why.
Put it next to a Submariner and Speedmaster and it couldn’t look more different.
Square case. Roman numerals. Exposed screws. That unmistakable Cartier design.
And that’s exactly why I’d keep it.
The further you get into watch collecting, the less appealing a box filled with ten variations of the same steel sports watch becomes.
The Santos changes the mood completely.
It can look smart with a shirt, relaxed with a T-shirt and distinctive without shouting for attention.
If I sold it, I suspect I’d eventually end up buying another one.
That’s normally a good sign you should have kept the first.
4. Tudor Black Bay 58
The watch I’d actually wear everywhere
Some watches become special because you’re afraid to wear them.
The Black Bay 58 is almost the opposite.
This is the watch I’d want for holidays, weekends, travelling and all the occasions when I don’t particularly want to think about what’s on my wrist.
At 39mm, it has the vintage-inspired proportions that helped make it such a favourite among enthusiasts, while 200 metres of water resistance gives it the practicality you’d expect from a modern dive watch.
More importantly, it has character.
Tudor has managed to create something that clearly draws on its history without simply feeling like a cheaper Rolex.
That’s why I’d struggle to sell one.
Not because it’s necessarily the most important watch in the box.
Because it might become the one I wear most.
5. Grand Seiko Spring Drive
The watch I’d keep for the movement alone
Every collection needs something a little nerdy.
For me, that would be a Grand Seiko Spring Drive.
The finishing is beautiful and Grand Seiko produces some extraordinary dials, but it’s that seconds hand that would keep me coming back.
Instead of ticking around the dial in the way you’d expect from a conventional mechanical watch, Spring Drive creates an almost perfectly smooth glide.
You can explain it.
You can watch videos of it.
But it makes far more sense when you see one moving on your wrist.
And that’s exactly the sort of thing I want from a collection.
The Submariner gives me the icon.
The Speedmaster gives me history.
The Cartier gives me design.
The Tudor gives me an everyday watch.
Grand Seiko gives me something to geek out about.
What actually makes a watch a keeper?
It isn’t resale value.
It isn’t rarity.
And it certainly isn’t what somebody on social media tells you is collectible.
A keeper is simply a watch you continue reaching for.
Sometimes that’s because of the design. Sometimes it’s the history. And sometimes the watch becomes attached to a particular person, place or period of your life.
Those are the watches I’d be careful about selling.
You can replace the reference.
You can’t always replace the connection.
Which watch would you never sell?
That’s the question I’d really like to know the answer to.
For me, these five cover almost everything I’d want from a collection: history, design, practicality, great watchmaking and enough variety to keep things interesting.
Your five might look completely different.
And that’s exactly how it should be.
At The Watch Experts, our constantly changing selection of pre-owned watches means you never quite know what you’ll discover next, from Rolex and Omega to Cartier, Tudor, TAG Heuer and beyond.
Browse our latest pre-owned luxury watches and see if you can find your next keeper.
Just choose carefully.
Because the best watch you ever own might be the one you eventually wish you’d never sold.