I did a couple of t-shirts for New Relic a while back, the idea being that Peter Cooper could hand them out as swag. We wanted one to be fun & quirky, and one to be a bit more subtle. Have a look!
Ruby & Friends:
Ruby leading the way, with his rail-car of buds. Coffeescript is up to something behind him - not the most trustworthy fella. Everyones favourite hero, HTML5, came along for the ride while one SASS-y pig applies the daily lipstick. Finally, Bundlr tries to keep everyone running smoothly as they truck along.
Speaks partially to the combination of Ruby & coffeescript/Java, but mostly to the fact that programmers so adore their coffee.