What makes a watch collector tick?

For some, the allure lies in the intricate dial designs, the watchmaker’s dedication to craftsmanship, or the rich history behind a timepiece. For others, it’s the hefty price or the renowned brand name that captures their interest.

Take Lionel Messi, for example. The soccer icon created a buzz among watch enthusiasts when he was spotted wearing his estimated $2 million ‘Barbie’ pink Rolex while on the sidelines at an Inter Miami match this week.

I consider my own watch collection one of my most successful portfolios.

I’ve been a watch collector since I was 14. My first acquisition, an Omega Speedmaster Moonwatch, was bought in Switzerland. My vast collection has grown so large that I’ve lost track of just how many watches I own.

Though I do get use out of them, wearing one on each wrist and exchanging them three times a day – breakfast, lunch and dinner.

And while there are pieces in my vaults that cost only a few hundred dollars, it’s the luxury timepieces that are the crown jewels.

Here are my favorite watches worn by your favorite actors, athletes and musicians:

I’ve been collecting watches since I was 14 – my first, an Omega Speedmaster Moonwatch, was purchased in Switzerland

I wear one on each wrist and exchanging them three times a day – breakfast, lunch and dinner

Mark Zuckerberg’s ‘Piece Uniques’

Watch collecting is infectious – once you acquire one, you just can’t get enough.

That’s why I call it a ‘disease.’ And Mark Zuckerberg has it.

When I ran into him at President Donald Trump’s inauguration in January, he admitted that the collecting bug just hit him one day and he’s been hooked ever since.

In fact, the Meta mogul has grown his collection of unique timepieces to include a diverse array of watches, from a $120 Casio to a $900,000 Greubel Forsey Hand Made 1, which he flashed in a January Instagram clip.

Just this week, he flexed a striking purple DB28xs Purple Rain from De Bethune, with a price tag of $99,000, in another post on social media.

These aren’t your typical luxury watches. They’re connoisseur items – ‘piece uniques,’ to the well-trained eye – meticulously designed masterpieces made in extraordinarily limited quantities.

Acquiring one is not a matter of waltzing into Rolex and buying one from the case. They’re more like Hermes Birkins – hard to come by and you must earn it.

Some of these watchmakers only make one piece a month. Why should you be the owner of one and not the thousands of others on the waitlist?

Zuckerberg has a $900,000 Hand Made 1 Greubel Forsey, which he flashed in a January Instagram clip

Watch collecting is infectious – once you acquire one, you just can’t get enough

The horologists who craft these timepieces – Simon Brette, Roger Smith, FP Journe – want to sell to a person who treasures their horology. I waited over a year for my Simon Britt watch and paid two years in advance, but the wait was worth it.

These watchmakers don’t want to sell to someone who will flip the piece for a quick buck. That’s how you lose credibility as a collector, and why you’ll never see my personal collection on the resale market or at auction.

You need to be known worldwide as an honorable collector. Good thing for Zuckerberg, he’s already got the renown.

Leonardo DiCaprio and John Mayer: The Rolex Hounds

The ‘three horsemen’ of watches are Audemars Piguet, Patek Phillippe and, of course, Rolex.

While Rolex is the youngest of the three the Swiss watch brand has, in the 120 years since its founding, perfected one of the world’s most popular watches – the Daytona – and acquired a devout cult following of stars who sport their timepieces while sitting courtside or walking the red carpet.

John Mayer and Leonardo DiCaprio, for instance, are Rolex hounds – notorious for sniffing out the best and rarest timepieces. Between the two of them they have collected incredibly unique dials and envy-inducing vintage watches.

Earlier this year, DiCaprio wore an ultra-rare $51,000 white gold Rolex Le Mans Daytona to a Lakers game. The limited-edition chronograph from 2023 pays homage to the 24-hour race in France with a subdial that can track time for a full day – a tiny but impactful detail over which enthusiasts obsess.

This year, DiCaprio wore an ultra-rare $51,000 white gold Rolex Le Mans Daytona to a Lakers game

The Rolex ‘John Mayer’ Daytona, a watch nicknamed after the singer that was discontinued in 2023, earned its nickname due to the musician’s integral role in popularizing the piece

Then, there’s Mayer’s Daytona, a now discontinued timepiece crafted with 18k yellow gold and an emerald dial.

The watch, colloquially known as the ‘John Mayer’ Daytona, was discontinued in 2023 and earned its nickname due to the musician’s integral role in popularizing the piece.

In fact, Mayer – whose first luxury watch was reportedly a $10,000 Rolex Explorer II – is known for his vast and eccentric collection, which includes unique timepieces like the Rolex ‘Puzzle Dial,’ with a jigsaw design that features emojis in the date wheel. The singer previously disclosed that his vast collection of timepieces is worth ‘tens of millions’ of dollars.

Tom Brady’s Bespoke Timepieces

Michael Rubin’s annual Hamptons White Party doubles as a battle of timepieces for the celebrity watch aficionados – me included.

Last year, however, I thought I had it in the bag. I, of course, was sporting my hallmark double watches – wearing a Rolex Puzzle on one wrist and a Cartier Crash Skeleton on the other – a habit I picked up to tell both local and Abu Dhabi time simultaneously.

Little did I know I’d be trumped by my biggest competition: Tom Brady.

We both have an affinity for flashy timepieces, and the NFL legend rolled up in his one-of-a-kind Audemars Piguet. The ode to his Super Bowl wins was emblazoned with his name and put my wrists to shame.

He is known for his blinged-out watches – namely, his $740,000 Jacob & Co yellow sapphire Caviar Tourbillon, made with 18k gold, a leather band, 48.92 carats of sapphires and 1.32 carats of white diamonds. He sported another Jacob & Co creation at the E1 Monaco Grand Prix last week when he wore a watch described as the brand’s ‘most technically complicated yet.’

Tom Brady wore a $740,000 yellow sapphire Jacob & Co watch to the Super Bowl this year

Brady’s timepiece is made with 18k gold, a leather band and more than 300 diamonds

Again, it is a one-of-one timepiece – the Twin Turbo Furious Tom Brady Edition – priced at $650,000. Created out of forged carbon, the graphite-colored timepiece with a rubber band is more utilitarian than the flashy options in his arsenal.

But such glitzy watches were not always the hot accessory they’ve become. They were a rarity until relatively recently, but today you can’t help but notice the eye-catching jewels on the wrists of Hollywood greats – Brady included.

Timothée Chalamet’s Cartier Craze

Cartier wasn’t even on the lips of collectors 20 years ago, but now they clamor to get their hands on a timepiece from the French Maison.

The brand produces highly sought-after pieces – the Crash, the Tank, the Santos – and I’m fortunate enough to own a few. In fact, I bought a Cartier Panthere in 1986 to celebrate my first closed deal and even shed a tear when I finally acquired a platinum Skeleton Crash.

And it appears I’m not the only one with a penchant for Cartier.

Timothée Chalamet, new to the watch scene, regularly sits courtside at New York Knicks games rocking the latest or greatest Cartier timepiece. He recently flashed a $55,000 Tank à Guichet – a chic, simple piece typically reserved as a dress watch that he paired instead with a crewneck and cargo shorts.

He’s also previously rocked a diamond encrusted Cartier Crash – a watch that, depending on the style, costs hundreds of thousands of dollars and is easily identifiable for its oblong, crushed face.

What makes that piece so unique is its origin story: It was created after a round Cartier watch was involved in a car accident and brought into the store for repair. So the lore goes, the grandson of Cartier’s founder was so enamored by the utterly deformed dial that it inspired him to reproduce it – thus, the Crash, one of the most coveted watches in the world, was born.

When people eventually saw the design they went out of their minds – they just couldn’t wrap their heads around how the timepiece worked with its misshapen face.

At the 2024 Golden Globes, Chalamet rocked a diamond encrusted Cartier Crash – a watch that, depending on the style, costs hundreds of thousands of dollars and is easily identifiable for its oblong, crushed face

Meghan has the Cartier Tank watch that once belonged to Princess Diana 

The late Princess Diana’s wore a simple Cartier Tank Française, a yellow gold watch, which is infamous among enthusiasts and is easily recognizable because of its hallmark square face

And that’s the beauty of Cartier: their watches don’t just tell time, they tell a story. They’re pieces of art and history, which is often bestowed upon the watch by its wearer.

The late Princess Diana’s simple Cartier Tank Française, for instance, was a staple of her fashion. She wore it throughout the ’90s and, after her death, it landed in the hands of her sons, Prince Harry and Prince William.

Now, it graces the wrist of Meghan Markle – reportedly a gift from the Duke of Sussex.

The yellow gold watch, which even lacked baguettes, is infamous among enthusiasts and is easily recognizable because of its hallmark square face.

It’s a timepiece so iconic that it can be spotted from 20 yards away and, on the wrist of a woman, it’s like Lady Di herself has walked into the room.