Kevin O'Leary says he buys $29 Walmart jeans — but admits to spending $120 on a single pair of boxers

“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.”

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.