Dustinland is a popular web comic that published a comic called "The Theory of Hipster Relativity". It outlined that a Hipster is someone more hipster than you are. That comic was a viral hit on the Internet, and to take advantage of the publicity, we designed and are developing this iPhone app that allows you to build your own hipster, and determine just how much of a hipster you are.
The challenge was to sort and organize hundreds of clothing articles and outfits that would be layered differently, depending on the location of the body. Eventually through testing we opted to allow the user to select the location and type of article first, then select which artcle would go in that location. Also we had to go back and forth on the best sharing method for social media, which I don't think we really ever hammered out completely.
The app needed to feel comic-like, and stay out of the way of the visuals of the drawings themselves. So rather than make the buttons and interactive elements hand-drawn, we chose a simple white button style that would feel button-ish and not confuse users.