Kevin O’Leary, a Canadian investor and longtime Shark Tank personality, is no stranger to luxury. On Shark Tank, he’s as well known for his sharp suits and trademark red pocket square as he is for making deals.
But one part of his signature style raised eyebrows: the habit of wearing two ultra-expensive watches at once.
“People once told me wearing two expensive watches on Shark Tank made me look like a total jerk. I realized they were right. Timepieces aren’t just flexing metal. They mark the milestones that define our lives,” O’Leary wrote in a post on X.
He expanded on the idea in a video he shared, reinforcing the same realization: “Somebody came to me on Shark Tank and said, hey, you know, this thing you’re doing with two watches, both of them are so expensive, nobody can afford them. Some of them are one of a kind and nobody can even get one. And you’re coming across like a real asshole.”
He admitted, “I hadn’t thought of it that way.” That comment stuck with him. The person went on to say he should be inspiring young people to get into watch collecting.
To O’Leary, that meant showing how timepieces can celebrate life events, like starting a business or having a child, instead of just flexing wealth.
Now, his watch setup is a mix of aspiration and accessibility.
“I’m wearing a $350,000 piece on my right today and a $2,000 piece on my left,” he said. “They’re both titanium watches. They’re both beautiful. Some people prefer the $2,000 dial versus the $350,000, doesn’t matter.”
The Man Loves Watches, And He Has the Collection to Prove It
O’Leary is deeply into watches, and his collection reflects that. Over the years, he’s shown off timepieces like these:
- Rolex Daytona “Panda” 116500LN — A popular stainless steel model with a black ceramic bezel, going for about $35,000.
- Rolex Daytona “Eye of the Tiger” 116588TBR — Covered in gold and diamonds, this flashy model sells for more than $200,000.
- Patek Philippe Aquanaut Luce Rainbow 7968/300R — A gem-studded rainbow watch originally marketed to women, worth around $500,000.
- Patek Philippe Nautilus 5711/1A — A classic blue-dial piece made of stainless steel, valued near $113,000.
- Audemars Piguet Royal Oak Piece Unique — A rare skeleton-dial watch with ruby accents that could fetch up to $700,000.
- Rolex Day-Date “Puzzle Dial” 128238 — A playful, emoji-filled watch that swaps out day and date for feel-good words like “Hope” and “Love.”
He often swaps out the original straps for bright red rubber ones, adding a signature twist to high-end designs.
Of Course, They’re Insured
Wearing two watches that add up to more than most people’s mortgage doesn’t come without risks.
O’Leary gave a quick plug for his insurance company: “WonderCare, my insurance company, you know, I needed that for watches like this. I have to insure all these watches.”
Whether you think it’s over the top or aspirational, O’Leary’s current watch setup sends a clear message: milestone moments matter more than just the price tag.