"14. Craig Newmark   Position: Founder of Craigslist   Style Sins: To the surprise of no one, the guy who started Craigslist dresses like a guy who stalks Craigslist—wrinkled shirts, oversized blazers and a beret fetish (check his Twitter avatar, @craignewmark). There's a fine line between looking ""artsy"" and uncomfortable. Craig has stepped over it."
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