Kevin O'Leary's $1,000 Lesson: How His Mom's Chanel Jacket Shaped His Investment Mindset

Kevin O’Leary learned one of his biggest money lessons from his mom, Georgette. It all started with a Chanel jacket.

In his book “Cold Hard Truth on Men, Women & Money,” O’Leary describes how he noticed his mom wearing a classic Chanel jacket at a family Christmas dinner in the 1980s. He was shocked when she told him she had bought it 20 years earlier, in the 1960s.

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That jacket wasn't cheap. Georgette had saved up for a whole year to buy it, spending $500. That was a lot of money back then. But she knew something important: quality over quantity. That jacket lasted her two decades. And today, it could sell for about $1,000. “The perpetually fashionable Chanel blazer would fetch about $1,000 today,” O’Leary wrote.

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This lesson stuck with O’Leary. He started seeing everything he bought as an investment. He focused on quality and what it could be worth later. “Treat everything you buy as an investment,” he says. He spends his money like that to this day.

When his mom passed away in 2008, O’Leary became the executor of her estate, which included her luxury jacket collection. “Many of those coats were one-of-a-kind collectors’ items and they had massively appreciated in value,” he shared on LinkedIn.

But it wasn't easy handling the estate. “The women in my family fought like cats and dogs to get near her clothing,” O’Leary joked to CNBC Make It in 2018. “I had to beat them back with a stick to be fair about it.”

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O’Leary took his mom's lesson to heart. He's known for his high-end wardrobe. He proudly showed off a $2,800 Yves Saint Laurent jean jacket. Just like his mom, he's willing to spend more on quality. He sees it as a smart investment.

Over the years, O’Leary has shared other money tips, too. He warned couples not to mix their finances, advised against lending money to family and discussed the importance of not waiting too long to marry and have kids. But the lesson from his mom's Chanel jacket stuck with him the most. For O’Leary, it's not just about spending. It's about making smart investments.

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