Even for the most skilled dressers, assembling a killer outfit sometimes requires a little more inspiration than the average online shopping experience provides. Enter Roxana Altamirano, the genius behind Nerd Boyfriend, the style blog that offers step-by-step instructions for re-creating ensembles worn by icons ranging from Richard Gere to the Rolling Stones. Now she's guest blogging on details.com every week. Have a hero you want to see featured? Leave a note in the comments and we'll see what we can do.
As David Shayne, a struggling playwright determined not to sell out, Cusack plays the typical Woody Allen character and gives us a glimpse of the director's dream 1920s wardrobe in the process. A traditional Norfolk tweed jacket, round metal glasses, and a horizontal striped tie are pitch-perfect representations of an obsessive artist trying to stay grounded in an exaggerated, absurd world.