Kevin O'Leary's Pricey Underwear: A Study in Contrasts Kevin O'Leary, the Shark Tank investor known for his frugal ways, recently showcased his $29 Walmart jeans on Instagram.
The move sparked surprise not because of his penny pinching, but because it starkly contrasts with another aspect of his spending habits.
In a 2018 interview, O'Leary revealed he pays $120 for a single pair of Egyptian cotton boxers from Zimmerli of Switzerland. Adjusted for inflation, this would be equivalent to around $160 today.