One of my favorite television shows is HBO's Flight of the Conchords. While the show is hysterically funny with its quirky musical comedy, I love the two main characters' sartorial style.
Jemaine Clement sports a pair of retro 70's style pork chop sideburns and dark-framed eyeglasses. Bret McKenzie has a slightly more hipstery style and often wears sweatshirts with silkscreened animals on them. (Very reminiscent of Stella McCartney for Chloe's Wild Horses show!) Overall, they sport a type of effortless "geek chic" that I find charming. Here are some examples.
Boys, try a take on "geek meets hipster chic" with the outfit below.