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Spend five minutes watching Shark Tank and you will spot it: Kevin O'Leary making a point with both hands, a watch riding each wrist, both almost always on bright red straps. It is not a wardrobe accident, and it is not only a billionaire's eccentricity. The double-wrist habit is part logistics, part personal brand — and it belongs to a man who genuinely loves watches and holds strong opinions about every one of them. Here is why Mr. Wonderful wears two watches, what is actually in his collection, and how to pull off the look without a Shark's net worth.
The Short Answer
O'Leary has explained the habit in interviews over the years, and it comes down to two things. First, practicality: he keeps one watch set to home time and the other to wherever his business is happening — a poor man's GMT, worn by a rich man. Second, identity: the red straps are a deliberate signature, matching the branding he has built for decades. The watches themselves rotate through one of the most serious collections on television.
Reason 1: Two Time Zones, One Pair of Wrists
O'Leary's schedule is famously split between cities — Boston roots, a Miami home base, Toronto shoots, and constant flights in between. A GMT watch solves that problem with a fourth hand, but O'Leary's solution is simpler and more visible: one watch per time zone, one per wrist. He has joked that one wrist tells him what time it is where he is standing, and the other tells him what time it is where the money is. For a man whose calendar runs on market hours and production schedules, the redundancy is genuinely useful rather than theatrical.
There is precedent for the setup. Fidel Castro famously wore two Rolexes on one wrist to track Havana and Moscow time simultaneously; General Norman Schwarzkopf wore two during the Gulf War for the same reason. O'Leary's version — one watch per wrist — is simply the more comfortable interpretation of an old military and diplomatic habit.
Reason 2: The Red Strap Is the Brand
The second reason is pure Mr. Wonderful. O'Leary has spent decades building a personal uniform: dark suit, white shirt, red tie or pocket square — and red watch straps. He swaps red straps onto nearly every watch he owns, from a Rolex Daytona to a Patek Philippe, turning a collector's rotation into a trademark. It is deliberate visual consistency, and it works: you can identify his wrists in a photograph before you can identify his face.
There is a collector's logic underneath the branding, too. Wearing two watches doubles the wrist time a collection gets. When you own more great pieces than you have wrists for, double-wristing is the enthusiast's workaround — and O'Leary's collection is deep enough to justify it.
Inside Kevin O'Leary's Watch Collection
Rolex Daytona — the Signature
The watch most associated with O'Leary is the Rolex Daytona, almost always worn on a red strap instead of the steel bracelet. The Daytona is the chronograph of choice for people who could buy anything — waiting lists, resale premiums and all — and O'Leary wears his constantly, on and off camera. If you are wondering what one costs and why it is so hard to find at retail, our guides to what a Rolex is actually worth and why Rolex is so hard to buy cover the real numbers.
Patek Philippe Nautilus
He has also been photographed in a Patek Philippe Nautilus — the steel luxury sports watch that trades hands above its retail price by multiples. The Nautilus is the insider's flex: less flashy than a Daytona to the untrained eye, more expensive in practice, and the piece other collectors notice first.
Audemars Piguet Royal Oak
Completing the holy-trinity pattern, O'Leary has worn Audemars Piguet Royal Oaks, including chronograph versions. Gerald Genta's octagonal design is the boldest of the three great steel sports watches — a fitting choice for a man who makes his living being the loudest voice in the room.
The Rest of the Rotation
Beyond the trinity, his rotation has included pieces from Omega, Jacob & Co. and other high-end houses — nearly all of them eventually fitted with the signature red strap. The through-line is not brand loyalty; it is a collector buying canonical references and then personalizing them until no one else could mistake them for theirs.
Is Wearing Two Watches Actually Practical?
For the rest of us, wearing two watches is unusual but not crazy. The legitimate use cases have been around far longer than Shark Tank:
- Dual time zones without a GMT — one watch on home time, one on local time, and zero bezel math at 30,000 feet.
- Smartwatch plus mechanical — health tracking on one wrist, craftsmanship on the other. Quietly the most common modern double-wrist setup.
- Redundancy — divers and pilots have doubled up for decades; a backup watch is cheap insurance when the first one floods or dies.
Get the Double-Wrist Look on Any Budget
You do not need a Daytona to run the two-watch play. You need one good watch, one purpose watch, and — for the full O'Leary effect — a red strap. Three picks that cover the spread:
Seiko 5 Sports GMT — the Two-Time-Zone Starter
The affordable answer to the two-time-zone problem is a proper GMT, and the Seiko 5 Sports GMT family is the entry point collectors actually respect: an automatic movement, 100 m of water resistance, and a 24-hour hand that tracks home time at a glance. One of these can replace the entire second wrist if you want the function without the theater — check the listing for the current price.
Red FKM Rubber Strap — the O'Leary Signature Move
The cheapest way to channel Mr. Wonderful is his actual signature: the red strap. A quality FKM rubber strap in bright red costs little, shrugs off sweat and salt water, and converts any watch in your drawer into the O'Leary uniform. Twenty minutes and one spring-bar tool — instant trademark.
Casio Duro — the Second-Wrist Beater
If you are going to wear two watches, one of them should be a piece you never worry about. The Casio Duro is the consensus choice: 200 m water resistance, a real timing bezel, and quartz reliability for the price of a decent dinner. It is the second wrist that lets the first one stay precious.
How to Pull Off Double-Wristing Without Looking Silly
- Differentiate the pair — a diver plus a dress watch reads intentional; two near-identical watches reads like you forgot one was on.
- One per wrist, never stacked — O'Leary wears one on each wrist, and so should you.
- Match the straps, not the watches — coordinated straps (his are all red) make two different watches look like a decision rather than an accident.
Frequently Asked Questions
Why does Kevin O'Leary wear two watches?
Practicality and branding. He keeps one watch on home time and one on local time as a constantly traveling businessman, and the ever-present red straps make the habit part of the Mr. Wonderful uniform. He has explained both reasons himself in interviews.
What watches does Kevin O'Leary wear?
His known rotation includes a Rolex Daytona, a Patek Philippe Nautilus, Audemars Piguet Royal Oak models and pieces from Omega and Jacob & Co. — nearly all worn on his signature red straps. The Daytona is the watch he is photographed in most.
Is wearing two watches pretentious?
It is conspicuous, certainly — and for a television personality, that is partly the point. For everyone else, the smartwatch-plus-mechanical combo has quietly normalized double-wristing. Done with two clearly different watches, it reads as enthusiasm rather than affectation.
The Bottom Line
Kevin O'Leary wears two watches because one tracks home and the other tracks where the deal is — and because red-strapped double-wristing became part of a carefully built personal brand. Steal the logic, not just the look: a GMT or a second beater watch, one red strap, and the confidence to commit. Browse the rest of our guides at The Watch Goat for the watches worth doing it with.