The best WWDC shirts are the ones issued to Apple engineer employees. Not all employees get to go to WWDC (after all, someone has to get iCloud up and running) and so these are rather prized shirts, perfect for sashaying through Caffe Macs on your quest for that perfect burrito.
Back in 2007, the shirts had a subdued, Great Recession-worth humbleness to them.
By the time WWDC 2008 came around, iPhone development by third-parties was in full swing, and the App Revolution was underway.
Perfect timing for a little location-based t-shirting:
Even if you moved around Moscone Center, the Apple Engineer WWDC Tshirt App knew where you were! Amazing.
WWDC 2009 gave us a play on the app icons now familiar to the eyes (and thumbs) of Apple developers everywhere:
Kind of like a ransom note, except in Objective-C. Bonus points if you know where each letter icon comes from.
WWDC 2010 kept the theme going, except this time in a more iPhoneesque layout:
Have a great show next week!