Kevin O’Leary Watch Collection

Jaeger LeCoultre Reverso on Kevin O' Leary

Kevin O’Leary’s Watch Collection

For venture capitalist and Shark Tank judge Kevin O’Leary, even watch collecting is serious business. Known for his blunt assessments and tough advice to entrepreneurs, he also has a few guiding principles when it comes to collecting watches.

For one, he wears all his watches at least once a month. Like a true entrepreneur, he believes watches are meant to be worn instead of being kept in a vault.

O’Leary is also known for making a statement through his watches. He often wears them with a red leather bracelet; and his shirts and suits have a half-inch allowance at the cuff to give you a peek of his watch.


Here are some of the Shark’s favorite watches:


Rolex Daytona Ceramic Bezel


Rolex Cosmograph Daytona Ceramic Bezel


The Rolex Daytona ref 116500LN was much awaited by watch fans. It combines the classic look of the stainless steel Daytona with the Cerachrom ceramic bezel – making the bezel less prone to scratching and fading.

Kevin owns both the black dial and white dial variants of the 116500LN, but instead of the Oyster bracelet that comes with them, he has swapped it out for his favorite red strap.


Rolex Submariner Blue Dial Bezel


Rolex Submariner Steel Yellow Gold Blue Dial


Kevin counts the Rolex Submariner as one of his go-to timepieces. While the Sub was initially developed for diving, many fans like Kevin have taken to wearing it during business or formal functions.

He wears the striking variation of Rolesor stainless steel and yellow gold model, matched with a vibrant blue dial and bezel.



Rolex Seadweller 50th Anniversary Steel Mens Watch, which comes with a red SEA-DWELLER lettering. On his right hand and wrist are the Rolex Cosmograph Daytona Ceramic Bezel models.
Here, we see Kevin showing off his Rolex watches. At left is the Rolex Seadweller 50th Anniversary Steel Mens Watch, which comes with a red SEA-DWELLER lettering. On his right hand and wrist are the Rolex Cosmograph Daytona Ceramic Bezel models.


Panerai Luminor 1950 Acciaio


Panerai Luminor 1950 Acciaio


Another favorite of Kevin’s is his Panerai Luminor Acciaio. The eye-catching 47mm watch comes with a cushion shaped case and circular crown guard, and is made even more striking when paired with his signature red strap.

This watch is outfitted with Panerai’s signature “sandwich” dial, where a luminescent background is sandwiched between the dial’s surface and the movement.


Cartier Roadster Silver Dial Red Strap


Cartier Roadster


One of Kevin’s first watches ever is the dressy Cartier Panthere, which unfortunately was stolen from him. These days, his Cartier watch of choice is the Cartier Roadster.

The Roadster, as it’s name suggests, was inspired by sports automobiles from the 1950s – hence its tonneau-shaped case that recalls the curves of vintage cars. Kevin adds a modern touch by pairing it with his signature red leather strap.


Jaeger LeCoultre Reverso


Jaeger LeCoultre Reverso


The Reverso is considered the first ever sports watch, having been developed in 1930 for polo players to use on the field. The Reverso’s geometrical, swiveling case was meant to protect the timepiece from sporting blows.

These days, the Reverso is considered a dress watch and many men prefer to wear it with a suit. The rectangular case fits nicely under the cuff and adds the right amount of sophistication.



Patek Philippe Nautilus 5711
One of Kevin’s latest acquisitions is the Patek Philippe Nautilus 5711. This particular model is a stainless steel watch that comes with a blue, horizontally embossed dial. It has an eight-year waitlist, so Kevin was over the moon when he finally got one! (photo: Patek Philippe)




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