Super Bad!

Despite his characterization of Gossip Girl as "inspirational" (and his fear of horses), we're giving Hassan's here look a perfect 10.0 score. Sure, one can always get more crisp or creative, but -- with a few minor accessory changes -- this uniform would put you at the top of the class in any setting from New York to Milan. With a nod toward better-dressed generations, it represents the height of modern sartorial wit and charm. (Pick up your own Aquascutum double-breasted suits and jackets at Bloomies.)