When: 5 years ago
Where: a gift from Mike, bro-in-law, originally from threadless.com
Why: First, it's a pun (the communist party)--I like the puniness of it. I got it when I lived in small town Idaho, and I wore it as anti-conservative backlash. People were already telling me I was a communist, so, I might as well wear something that says I am. Yeah, people always get it right off. It's pretty clever.
One of my bosses from my last job (TV), he's a very outspoken right-wing (Canadian), and his family came from the Ukraine. This shirt really offended him. He didn't like it all. I was kind of surprised; I'd never gotten that strong a reaction. It had never made anyone mad. He actually pulled me aside to ask me, "But, you're not really a communist? Because you know they're bad news."
Honestly, I'm getting rid of the t-shirt, but not because of it's potential for offense, only because it's time to edit my t-shirt collection.