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Slide 9 of 26

Calvin Klein Jeans Ads

The ads for Calvin Klein Jeans launched Kate Moss's international career in the early '90s. Soon enough, his racy black-and-white commercials gave way to the "heroin-chic" runway phenomenon. Now, the Kardashian-Jenner clan stars in the brand's 2018 campaign, which is still just as iconic.

Image Source: Getty / Tom Wargacki