"Really talking retro": Shark Tank investor Kevin O'Leary reveals his latest top 3 watch picks

Kevin O'Leary, a Shark Tank investment guru, recently revealed his new top three watch recommendations in an Instagram video on February 20, 2025. He featured the Mühle Glashütte SAR, the Oris Kermit, and the Rado Diastar, and named the Rado Diastar as his number one.

"You're really talking retro when you walk around with this, but it's been modernized," he said praising its mix of retro style and contemporary functions.

His selections reflect a mix of design and functionality, adding to his known appreciation for high-quality timepieces.

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Shark Tank investor Kevin O’Leary’s watch picks

In his Instagram post, Kevin O’Leary reviewed several watches with a retailer before narrowing down his top three selections. He first acknowledged the Rado Diastar, emphasizing its design.

The Shark Tank investor said that it was "just a spectacular piece," adding that he loved it and loved to "look at that." The watch retailer noted that the selection process was tough, and O’Leary agreed, highlighting the difficulty of choosing between high-quality options.

The entrepreneur selected the Oris Kermit, referring to it as an interesting piece. The Shark Tank investor confirmed his decision by describing it as "pretty interesting."

The final selection process led to the inclusion of the Mühle Glashütte SAR. After finalizing the top three, O’Leary declared the Rado Diastar as the leading choice. The Shark explained why he liked it, adding that it was "retro yet striking," and "modernized yet a unique dial." He noted that in that particular watch, "the case is the dial."

O’Leary then discussed the possibility of modifying the Rado Diastar with a red band. He said that it would be a challenge to fit a red band onto the watch but suggested that it could complement the design by matching the logo’s red detailing. The retailer acknowledged the challenge but O'Leary said that it would look good.

"But it would look good. You're picking up the logo in the red. So it's very nice," the investor said.

His selections demonstrated his interest in watches that merge design history with modern elements.

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A look inside O’Leary’s watch collection

Kevin O'Leary's love for watches is not just limited to his recent choices. Wrist Enthusiast reported that among his high-ticket watches is the Patek Philippe Nautilus 5711. He had been spotted with this watch and its market price went up in 2019 after that.

The Shark Tank investor has also had a Rolex Daytona 116500. Wrist Enthusiast said he subsequently auctioned this item in 2019 for $56,700, with proceeds going to charity. The magazine reported his association with high-end watches, reporting that his collection has watches with good resale value.

He has also been seen sporting the Rolex Daytona "Eye of the Tiger," a watch whose bezel is surrounded by diamonds. He was seen sporting this model with his red signature strap on Shark Tank in 2022.

Another of his watches is the Rolex GMT-Master II Pepsi, which he was spotted wearing on Mornings with Maria. Wrist Enthusiast pointed out that this model, which initially sold for $10,750, had appreciated greatly on the resale market.

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O'Leary's latest Instagram post is in line with his previous selection of watches that possess both aesthetic appeal and long-term value. His focus on distinct appearances, such as the Rado Diastar, also reflects his overall interest in usually distinctive watches.

Watch Shark Tank on ABC every Friday at 8 pm ET and is also available to stream online by viewers through Hulu.