Kevin O’Leary wears two watches mainly because he’s a hardcore watch collector who wants to keep more of his pieces in active rotation, track multiple time zones for global business, and make a personal style statement about what watches mean to him.

Quick Scoop: The Short Answer

Kevin has explained at events that he owns so many watches that wearing more than one helps ensure they all get actual wrist time, and he even says that if you don’t wear a watch, it “loses its soul.”

He also uses multiple watches to stay connected with investors and teams across different time zones, so two watches can be both a flex and a practical tool for global business.

The Story Behind The Two Watches

Over the last couple of years, people started noticing him “double‑wristing” at conferences and on TV, especially around fintech and investing events.
At one such event, he directly told the audience that he wears multiple watches now because he has so many and doesn’t want them sitting in a safe unused.

He’s described watches almost like living objects in a collection: if you don’t wear them, they lose their soul.

That idea turned into a talking point for him, and wearing two at once became part of his on‑brand persona: the ultra‑serious investor who’s also a watch obsessive.

Practical Reasons (Not Just Flex)

Several watch-focused write‑ups and interviews break his habit down into a few practical motives:

  • Rotating through a large collection so more pieces see daily use.
  • Tracking multiple time zones (for example, New York plus Dubai or other financial hubs) using different complications.
  • Using different watch functions at once, like a simple three-hander on one wrist and a GMT or other complication on the other.
  • Treating watches as both tools and investments, similar to modern art: owned, worn, and appreciated, not just stored away.

In other words, it’s not just “two fancy watches for show” in his framing; he positions it as a blend of utility, collecting philosophy, and image.

How Fans and Forums See It

Online watch and finance communities are split, which fuels the ongoing forum discussion and keeps “why does Kevin O’Leary wear two watches” a trending topic now and then. Common viewpoints you’ll see:

  1. “Serious collector” angle
    • Some watch fans argue that if anyone’s going to double‑wrist, it makes sense it’s a high‑end collector with a huge rotation, especially someone working across time zones.
 * They see it as an extension of watch culture: you love them, you wear them, sometimes more than one.
  1. “It’s just a flex” angle
    • Others think wearing two expensive pieces on TV is over the top and mainly a branding move—Mr. Wonderful signalling wealth and taste.
    • Even O’Leary himself has acknowledged people once told him wearing two expensive watches made him look like a “jerk,” which he’s used to pivot into a message about design and accessibility (pairing a very high-end piece with a much more affordable one).
  1. “Practical but exaggerated” angle
    • A more middle stance says: yes, multiple time zones and complications are real use cases, but you could solve that with one good GMT watch.
    • From that view, the second watch is less about necessity and more about storytelling, marketing, and personal quirk.

Trending & “Latest News” Flavor

Recently, coverage and social clips tend to frame his double‑wristing as:

  • A talking point in interviews where he discusses wearing several pieces in a short rotation, sometimes saying he can go through roughly a dozen watches every couple of days by rotating multiple per day.
  • A visual hook on social posts where he contrasts a very expensive luxury watch on one wrist with a more accessible piece on the other, reinforcing his message that great design isn’t only for ultra-wealthy buyers.

So when people ask “why does Kevin O’Leary wear two watches,” the current narrative blends:

  • Collector philosophy (“watches lose their soul if they’re not worn”).
  • Business practicality (multiple time zones, global teams, investors).
  • Personal branding and style (recognizable, slightly controversial TV persona).

Mini FAQ

Is there one “official” reason?
Not exactly. He’s publicly talked about owning many watches and not wanting them to sit unworn, and watch writers add the time‑zone/complication angle on top of that.

Couldn’t he just use a GMT watch?
Yes—many GMTs track multiple time zones, but part of the point for him is to enjoy more of his collection on the wrist, not just maximize efficiency.

Is this just marketing?
It definitely functions as a visual trademark and talking point, even if he also believes in the functional and emotional reasons he gives.

TL;DR:
He wears two watches because he’s a serious watch collector who wants to give more of his watches “wrist time,” believes unworn watches lose their soul, needs to track global time zones, and has turned the double‑wrist look into a deliberate part of his on-screen and online persona.

Information gathered from public forums or data available on the internet and portrayed here.