5. Mark Zuckerberg
This 27-year-old billionaire takes a lot of flack for the real and perceived sins of his little dorm-room project called Facebook, but he doesn't let that get in the way of living a charmed lifestyle. Zuckerberg re-invented the tech entrepreneur's dress code in his own hyper-casual image, showing up on a day-to-day basis in flip-flops and a hoodie, and taking fuck-you meetings with would-be business partners clad in his favorite pajama bottoms. As if the attire didn't make things clear enough, the supremely self-confident young executive famously telegraphed his privileged status on a set of custom business cards. They read: "I'm the CEO, bitch."