Rich Hilfiger
Bearing such a recognizable stamp as Hilfiger has always been quite the cross to bear for one, literal, Mr. Rich. So much preppiness to be undone. So how does one scrub away all that red white and blue? Well, becoming a rapper is a fair start. Dying your hair green, getting arrested multiple times, and tattooing yourself into Jared Leto's version of The Joker also helps.
While he once dated British pop star Rita Ora (after Rob Kardashian), @rickyhil has remained out of the tabloids for some time now, though his 47,300 Instagram followers seem to be keeping tabs on him.
Funnily enough, he joined the family business this year and launched his own "fashion" label, Tango Hotel, a line of men's underwear and tees. We're sure dad approves of this endeavor, at least.
[Photo via @rickyhil]
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