Show (Air Dates): 30 Rock (2006-present)
Actor: Judah Friedlander

The trucker hat died in 2002, right? Not in Frank's world. The TV writer's signature slacker wardrobe (as well as Judah's off-set style) consists of square-framed glasses, baggy tees, and those chunky foam caps printed with random phrases, such as Bigfoot Expert, Best Dressed, World Champion, and Time Travel Agent. If you share his sense of ironic humor and style, you can buy into it directly at his online shop.