Kevin O’Leary has made his frugality almost as famous as his bluntness. The Shark Tank investor recently went viral standing in a Walmart aisle, comparing Bounty paper towel pack sizes and showing off the $29 black jeans he wears regularly. “Inflation affects all of us,” he said in the Instagram video. “Saving dough is the name of the game.”
But there’s a category where Mr. Wonderful doesn’t save dough, and it will surprise you.
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“My underwear cost $120 each,” O’Leary told CNBC Make It in 2018. “I love them.”
He buys Egyptian cotton boxers from Zimmerli of Switzerland, which has been handcrafting underwear since 1871.
Adjusted for inflation, that $120 he spent eight years ago is actually around $160 today.
O’Leary also pays $80 for haircuts, getting one every 10 days. “I don’t have that many, so I want them to have a personal relationship with every hair,” he joked.
The logic behind the contradiction
The contrast between $29 jeans and $120+ underwear may sound like a contradiction, but to O’Leary, it’s a strategy. He’s willing to spend on things that directly affect how he looks and feels, while refusing to overpay for things that don’t.
“I invest in looking great all the time,” he told CNBC, by paying for great clothing and shoes, and frequent haircuts.
Something he won’t spend on: pricey coffee. “Do I pay $2.50 for a coffee? Never, never, never do I do that,” he told CNBC. “That is such a waste of money for something that costs 20 cents.”
The underlying framework is one he’s learned to apply to every purchase. “Anytime I pick up something I’m going to buy, I say to myself, ‘Do I really need this?'” he explained, adding that if he opts out, that’s money going towards investments instead, to “make money every year for [him] while [he’s] sleeping.”
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The bigger financial philosophy
O’Leary’s selective spending is part of a broader wealth-building philosophy rooted in discipline and compound growth. In an interview with The Diary of a CEO, he said: “I can’t stand it when I see kids that are making 70 grand a year spending $28 for lunch. I mean that’s just stupid.”
His point isn’t the $28 itself — it’s what that money could become. “Think about that in the context of that being put into an index and making 8% to 10% a year for the next 50 years,” he said.
He also recommends a simple closet audit: look at how much of what you own you actually use. O’Leary suggests most people regularly use about 20% of their wardrobe while the other 80% sits untouched — showing how money gets wasted on things that felt necessary in the moment but weren’t.
His solution is automatic investing — specifically, putting aside 15% of your salary before you have a chance to spend it. “If you’re making $70,000 a year and you put 15% aside from when you’re 25, you’ll have over a million and a half dollars if you just invested it in the stock index in the S&P 500,” he explained. “That’s what history has told you.”
His mother modeled this approach — investing 20% of her weekly earnings in dividend-paying stocks and bonds for 55 years, never touching the principal. He saw it and knew it was how he’d invest for the rest of his life.
What the data says about spending and wealth
O’Leary’s framework is backed by research. According to Northwestern Mutual’s 2025 Planning & Progress Study, 79% of American millionaires describe their wealth as self-made, compared to just 12% who inherited it. The 2026 edition of the study found that 53% of Americans now describe themselves as “disciplined” financial planners — a two-year high after hitting a record low of 45% in 2024.
Ramsey Solutions’ National Study of Millionaires — which surveyed more than 10,000 millionaires — found that 94% live on less than they make, and that one-third never earned a six-figure salary at any point in their career.
As O’Leary put it to CNBC: “The biggest mistake in life people make is their lifestyle — their lavish lifestyle is more than they are actually making. The best thing would be to only spend 90% of what you bring in, and invest the other 10% for the future.”
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This article originally appeared on Moneywise.com under the title: Kevin O’Leary says he buys $29 Walmart jeans — but admits to spending $120 on a single pair of boxers
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