Some interesting facts about the shirt scandal: It was a running joke at their office to have this particular guy wear incredibly tacky buttondowns, something the whole office contributed to. Dragon detailing, 3 wolves, you name it. The mentioned shirt was actually made for him by a female friend of his who thought it would be hilariously tacky.
Dude wasn't trying to make a point, he was trying to wear the crappiest shirts he could for his coworkers to make them laugh, and he got completely fucking slammed for it.