Lucky for my office, I have experience designing t-shirts (from 6 years ago in high school when I designed Carnival and Skip Day shirts). Some lessons I learned: 1) The more colors you use the more expensive your t-shirt will be 2) Intricate T-shirt designs don't always look the way they do in your photo. Conscious of these requirements and avoiding a design that looks generic non-profity, I decided to make shirts inspired by MAD MEN!
Yes, I am obsessed with Don Draper, but how funny (I mean 'cool') would it be to see 700+ people in skinny black ties and pearls getting all sweaty and dirty from gardening and painting murals. I agree the one lame factor of the design is that they are a bit hipster/emo-like, but that is not what I am going for. I am going for playful, outrageous... 60s. Girls could have colored in the pearls with markers.
The winner was announced last Friday, and I didn't win (big surprise). I heard the Mad Men shirt came close to being a finalist, which makes me really happy that someone else shares my sense of humor or is also crazy.
Here are the Mad Men shirt designs:
I might have been more successful if I didn't restrict myself to cutting costs by using fewer colors and creating images that were solid shapes. Maybe next year, and hopefully by then the iEverything will be out.