3. Name: Reid Hoffman

Position: Co-Founder and Chairman of LinkedIn, investor in Digg, Flickr

Why he’s the worst-dressed: Hoffman hasn’t really offended the style-police too much, but don’t you think he looks like your very own neighborhood’s friendly cable-operator, or computer fix-it person? Loose T-shirts topped with even looser jackets are hardly the attire for a CEO, and much lesser of one who heads LinkedIn (i.e. the world’s professional social network).