Why Does Kevin O’Leary Wear Two Watches?

Why Does Kevin O’Leary Wear Two Watches? The Story Behind His Iconic Double-Wristing

Kevin O’Leary, best known as “Mr. Wonderful” from Shark Tank, is a billionaire investor, entrepreneur, and outspoken personality. But beyond his business acumen, one of the most intriguing things about O’Leary is his habit of wearing two watches at the same time. If you’ve ever seen him on TV or in interviews, you’ve probably noticed his signature double-wristing style—but why does he do it?

In this guide, we’ll uncover the real reason Kevin O’Leary wears two watches, his favorite watch brands, and whether this trend has any practical benefits.

The Real Reason Kevin O’Leary Wears Two Watches

At first glance, wearing two watches might seem like a fashion statement, but for Kevin O’Leary, it has a deeply personal meaning.

O’Leary has shared in interviews that he started wearing two watches in honor of his late mother. His mother played a crucial role in his life and taught him about the value of money, investing, and financial discipline. When she passed away, he started wearing her watch alongside his own as a tribute to her memory.

A Symbol of Legacy and Family

According to O’Leary, his mother’s watch represents timeless wisdom, financial knowledge, and the lessons she passed down. Instead of keeping it locked away, he chooses to wear it daily as a constant reminder of her influence on his success.

📌 Key Takeaway: Wearing two watches isn’t just about fashion for Kevin O’Leary—it’s a sentimental gesture that keeps his mother’s presence with him at all times.

What Watches Does Kevin O’Leary Wear?

Kevin O’Leary is a well-known luxury watch enthusiast, and his collection includes some of the most sought-after timepieces in the world. Here are a few of his favorite brands and models:

1. Rolex Daytona (Red Strap Edition)

One of O’Leary’s most iconic watches is the Rolex Daytona, which he customizes with a red strap to match his signature style. Rolex is known for its prestige, durability, and investment potential, making it a favorite among high-net-worth individuals.

💎 Learn More About Rolex Value: How Much is a Rolex Worth?

2. Patek Philippe Nautilus

O’Leary is also a big fan of Patek Philippe, particularly the Nautilus model. This watch is one of the most desirable luxury sports watches, known for its understated elegance and high resale value.

💎 More Patek Philippe Insights: Patek Philippe Nautilus Replica

3. Audemars Piguet Royal Oak Chronograph

The Audemars Piguet Royal Oak is another favorite in O’Leary’s collection. Designed by Gérald Genta, this watch is famous for its octagonal bezel and integrated bracelet. It’s a power statement that aligns well with O’Leary’s bold personality.

💎 Luxury Watch Buying Guide: Ultimate Guide to Buying a Bust Down Rolex

4. Other High-End Timepieces

Kevin O’Leary’s collection includes watches from brands like Vacheron Constantin, Richard Mille, and Omega, but he always customizes them with his signature red strap to make them uniquely his.

Is Wearing Two Watches Practical?

While O’Leary wears two watches for sentimental reasons, some people wear multiple watches for practical purposes. Here are a few reasons why someone might double-wrist their timepieces:

✔ Tracking Different Time Zones – Frequent travelers or global business leaders may wear two watches to keep track of time in different countries.

✔ Style and Fashion Statement – Some people wear two watches simply to stand out or showcase their collection.

✔ Digital vs. Analog – Some prefer wearing a smartwatch on one wrist for health tracking while keeping a luxury watch on the other wrist for style.

📌 Key Takeaway: While most people don’t wear two watches, it can be practical for those who travel often, work with multiple time zones, or want to blend technology with tradition.

Should You Wear Two Watches Like Kevin O’Leary?

If you’re considering adopting the double-wristing trend, here are some things to keep in mind:

✔ Make it Meaningful – If you have a sentimental reason, wearing two watches can be a powerful personal statement.

✔ Choose Complementary Styles – A dress watch and a sport watch can balance each other out rather than looking overwhelming.

✔ Stick to Your Brand – If you have a favorite brand like Rolex or Patek Philippe, double-wristing allows you to showcase more of your collection.

💎 Explore More Rolex Models: Presidential Rolex Review

Final Thoughts: The Meaning Behind Kevin O’Leary’s Two Watches

Kevin O’Leary wears two watches not as a fashion statement, but as a tribute to his late mother, who taught him the value of money and success. While his luxury watch collection includes Rolex, Patek Philippe, and Audemars Piguet, the watch from his mother holds the most sentimental value.

Wearing two watches may not be for everyone, but for O’Leary, it represents legacy, family, and financial wisdom. Whether you want to try double-wristing for practicality or personal reasons, there’s no wrong way to wear a luxury watch.

💎 Want More Expert Watch Insights? Check out our full collection of luxury watch reviews and guides at The Watch Goat.