Why Does Kevin O’Leary Wear Two Watches? 

If only we all had deep enough pockets to afford a dream watch whenever we fancied. Budget would be of no concern, and our watch collection would be virtually bursting at the seams – a timepiece for every scenario, every outfit, every day. 

That’s a reality for stars like Kevin O’Leary, successful Shark Tank investor and TV presenter (with a net worth of around (ah-hem) $400 million). The Canadian businessman can splurge on random luxury timepieces whenever his heart desires, rocking the two-watch-wearing trend and outright owning it. But why?

Kevin O’Leary doesn’t beat around the bush. Watch collecting is a disease, did you know? And once it gets under your skin, you have to live with it.

There’s no cure. At least, that’s how he describes his unapologetic addiction to flaunting some of the world’s most covetable timepieces against the sleeve of his $2,800 Yves Saint Lauren denim jacket. It’s simply not his fault. 

Watch addiction is an unimaginable force that sucks you down the horological rabbit hole at unstoppable speed, at least, if you have the budget for it in the first place. 

But despite the financial capacities that separate the business entrepreneur from people like you and I, he still has some great advice for enthusiasts from any walk of life, whether that be about which brands to invest your money in, the beauty of owning historically important watches, or avoiding buying crap. 

He even has his own views on watch etiquette and why he feels that wearing two watches is actually OK.

Who is Kevin O’Leary? 

Perhaps what acquainted Kevin O’Leary with the world of watches was the fact that he was a well-travelled child.

Thanks to his stepfather’s job, O’Leary got the chance to hop from one country to another, experiencing a diverse range of cultures, including Geneva’s watchmaking roots, whilst visiting the United Nations offices in Switzerland. 

By the time O’Leary landed back home from his world tour, the horological seed was already well and truly planted.

It also seemed the man was destined to make a ton of money, which conveniently coincided with his love of watches, enabling him to explore his passion for watchmaking to levels many people could only dream of. 

The man has always had a sixth sense for identifying areas of increasing value, seizing opportunity after opportunity, and the same can be said for his ability to collect watches, too.

First and foremost, Kevin O’Leary is a successful business investor. His first big break came when he invested $10,000 in an educational software company. That company went on to sell for $4.2 billion. Enough said. 

Then, there is O’Leary’s cheffing skills, which he puts to use on his YouTube channel, garnering a huge following for his role as “Chef Wonderful”, where he brings to life cuisines from all over the world through his love and knowledge of cooking.

Aside from being passionate about photography and knowing a thing or two about fine wines, you can also find O’Leary submerged in his love of music. 

He’s a keen collector of guitars and, over the years, has become an accomplished musician. As far as I’m aware, he can’t play more than one instrument at any one time, but he can certainly wear two watches.

Kevin O’Leary Is a Big Watch Fan

Kevin O’Leary is a keen watch collector with a fair few opinions to share on all things horology. His watch collection is very sacred to him. In fact, he has expressed wishes to be buried alongside his watches (it seems you can take it with you!). 

He doesn’t view his watches as assets, either. (Could he be the only loaded celebrity who actually sees the art and meaningful sentiment behind a watch for what it really is?).

His collection, which comprises novelties from the likes of Audemars Piguet, Grand Seiko, Patek Philippe, and Rolex, to name just a few examples, is split across several safes all over the world, and he won’t promote a single thing when filming Shark Tank. 

Even more endearing is that he claims he’ll never sell a watch, not that he’ll ever need to!

Kevin O’Leary spends his time sniffing out unique collectibles, the rare gems that only the affluent folk of society can afford, but he also has a lot of respect for brands like Seiko, which churn out large quantities of watches year by year. Indeed, it’s merely about a particular brand, as such. 

Moreover, it’s whatever watch conjures an emotive response within him and triggers a connection. Suffice to say, this man has been collecting luxury wristwatches for over 50 years, and lives by some important rules.

One, of course, is his right to wear two watches at the same time. Other advice includes buying watches to celebrate the small wins in life, no matter how insignificant. If you can, do it, he says. 

Any watch you buy to mark one of life’s milestones is a watch with sentiment and will therefore evoke some level of emotion when you wear it. Another piece of O’Leary’s advice is to invest in a big brand, if you can. That way, you can move up the horological ladder to where you eventually want to be.

According to the successful business person, you should also aim to diversify your watch collection wherever possible. In doing so, you can experience the whole gamut that the horological industry offers.

And, if you have the know-how and skill to understand the context behind a watch, you can use this experience when selecting historically significant watches. 

Lastly, his view on wearing two watches at any one time runs much deeper than simply owning too many watches. More specifically, his decision to do so stems from his need to keep in direct contact with his many investors.

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He uses his watches to retain open communication channels and uphold meaningful connections with his overseas teams. But you’re wondering which watches could possibly sit side by side with one another and still look good, right?

A Glimpse Inside Kevin O’Leary’s Watch Collection

It’s safe to say at this point that Kevin O’Leary doesn’t buy into hype watches. Moreover, he has a deep understanding of the world of horology.

He knows what makes him tick and prefers to spend his money on meaningful designs that either play a significant role in his day-to-day life as one of the world’s most successful business people, or those he has grown up with. 

Vacheron Constantin, for example, is a brand that has been in his life since the young age of just 14, hence he’s now the proud owner of the blue-dialed Overseas watch, which he loves very much. 

And the thought process behind putting two watches on in the morning does seem to follow some sort of method, too, usually starting with the “should I wear gold or steel” deliberation and working outwards from there (dial colour, strap material, and so on and so forth).

O’Leary wears everything from the Omega Speedmaster to the F.P. Journe Chronomètre Bleu. When pairing watches together, combinations including the Patek Philippe Nautilus and the Audemars Piguet Royal Oak often make an appearance as a duo. 

Both are highly covetable sports watches with mass appeal and a huge wrist presence. It has become imperative to O’Leary, particularly over the last few years, to restore the utility of a wristwatch to its full potential, especially following the advent of the smartwatch. 

O’Leary still considers watches a piece of art, but the fact that they can help keep track of New York time and Dubai time makes them even more indispensable when juggling multiple time zones like he does.

Why Are Watches So Important to Kevin O’Leary That He Wears Two?

Back in 2023, Kevin O’Leary garnered a lot of attention when he rocked up at the Benzinga Fintech Deal Day & Awards wearing two watches. When quizzed on the decision to do so, he simply replied that if you don’t wear a watch, it loses its soul. 

Clearly, the TV star has many watches to rotate within his collection, and this is one guaranteed way to ensure each one gets some wrist time.

But since then, we’ve discovered a lot about the man as a watch connoisseur and have come to understand that his watches mean much more to him than simply finishing off an outfit. 

New York and Dubai are where all the money is, so it makes sense that Kevin needs to juggle time zones in order to conduct important business meetings abroad, and part of that process is to navigate multiple time zones. So why not just wear a GMT, you ask?

Well, O’Leary is not the only one wearing two watches. The “double wristing” trend has been taken up by the likes of Richard E Grant and Prince William.

It’s not exactly a new concept. In fact, it’s been around for quite some time, with historical figures such as politician Fidel Castro and NASA Dr Edgar Mitchell among those who have adopted the trend. 

For all of the above, wearing two watches has been about managing two times at once. Fidel Castro wore a Submariner alongside a GMT, enabling him to track three time zones at once easily.

Likewise, Richard E Grant wore the Cartier Santos and a Breitling Navitimer at the 2023 BAFTAs to memorialize his late father, setting one watch to Eswatini time.

Is It OK To Wear Two Watches?

And here’s where one of the biggest disagreements amongst the watch-collecting community exists – is it OK to double wrist? It’s a practice more commonly seen when combining a smartwatch with a traditional analogue.

This way, a collector can still enjoy their classic timepiece while taking advantage of an entire suite of smartwatch apps and features. 

The divisive argument for whether you should wear two watches or not simply lies in whether one is broadminded enough to accept that it looks OK.

For some double wristers, wearing a smartwatch and a traditional wristwatch is not even the same thing, since one is more of a high-tech wrist-worn computer, and the other actually displays the time. 

Those people would argue that they’re simply wearing one watch.

Whatever way you look at it, wearing two watches is a personal choice, and the opinion on this topic varies from one collector to another. One thing is for sure, however. It’s not a common fashion choice, and a larger portion of watch enthusiasts are not doing it than doing it.

Reasons for opting out of the trend include the belief that wearing two watches can be cumbersome and will undoubtedly leave one watch redundant, since you only need to check the time on one dial.

Still, it’s a style choice for some, and it just so happens that some of the most devoted and affluent collectors are doing it.

Reasons Why People Wear Two Watches at the Same Time and How to Double Wrist Stylishly

As mentioned earlier, those who double wrist have their own personal reasons for doing so, just as some will prefer to wear their wrist on their right hand, rather than their left. 

The majority of evidence in favour of wearing two watches seems to lean towards the ability to track two or three time zones at once, while other reasons could be down to a collector owning too many wristwatches.

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Either way, if you were seriously contemplating wearing two watches like Kevin O’Leary does, there are things to consider and ways to do it…

It makes sense that wearing two watches of the same size can feel a little odd, almost like you’re trying to quell some OCD urge to balance weight and proportions out across both wrists. The often-desired way to double wrist is to wear two watches of different sizes. 

That way, one can dominate the other and become the main focal point of your attire, celebrating diversity. Others would argue that wearing two watches of the same size is better, since it’s pretty normal for one particular size to sit well on a person’s wrist. And since both wrists measure the same size, why should one wrist be unhappier than the other?

Before we move on, another argument for wearing two watches springs to mind whilst I write this. Creating contrast when double wristing is one thing, but you may require the use of two complications at the same time. Yes, this also circles back to O’Leary’s use of wearing two watches for timezone-tracking. 

He likes to be able to use a classic three-hander and a GMT watch at the same time. But suppose you’re measuring laps at the 24 Hours of Le Mans, but also need to know when to call home and wish the kids “goodnight”? If you don’t happen to own a watch that combines your two most important complications, there’s certainly an argument for wearing two watches at once.

So, Why Does Kevin O’Leary Wear Two Watches?

If you’re Kevin O’Leary, you believe that watches serve very functional purposes, even in today’s society. Yes, complications like the classic GMT allow you to track up to three time zones simultaneously (depending on the model), but if you have as many luxury timepieces as he does, why wouldn’t you utilize them simultaneously? 

He’s also a passionate watch collector, and no amount of convincing a connoisseur that they don’t need to wear a watch when they’re determined to, will sway them not to. 

He’s Kevin O’Leary – he can do what he likes! Being a passionate watch collector, he sees the value in supporting manufacturers that resonate with his values, and sometimes that may spark the urge to promote a brand if he likes them hard enough.

The businessman knows how to look cool and stylish, and let’s face it, he owns some of the most iconic watch designs in history. 

Lastly, O’Leary believes that you run the risk of your watches “losing soul” if you don’t wear them regularly enough. If anything, it’s nice to see someone as successful as him willingly getting the wear out of his watches, rather than buying a hype watch to wear as a one-time statement piece.

Conclusion    

Say what you will about Kevin O’Leary, but the man sure has good taste in watches, from elegant Vacheron Constantin complications to bold status symbols like the Royal Oak and Nautilus.

But his deep-rooted passion for intricate in-house design and authentic craftsmanship seems to set the Shark Tank star apart from other millionaires. 

For O’Leary, a watch has to tell a story or serve as an emotional link to his past endeavours to deserve a place in his ever-growing collection.

And if you were expecting to see some of his most prized possessions fetching thousands of dollars at auction one day, think again. He’s taking them with him, and he’ll be wearing two!