The Irony of the T-Shirt

My friend Nick has a favorite t-shirt that features Kelly Clarkson across the front. Nick is a comedian and former punk musician, 31 years old, bearded and graying, not tall or thin. He jokes that he looks like E.T. doing a headstand (which I still don’t quite get), and he is a magical mix of extreme egotism and extreme self-deprecation. I would not describe him as a hipster, though he most definitely falls into the trend of the hipster Ironic T-shirt. Hipsters (in my own observation) dress badly on purpose, pronouncing their independence and societal unification through this conscious choice of poor dress.  The trend in which the wearer silently voices “Hey, look at what I’m wearing! Isn’t it ridiculous? But you know I know it’s ridiculous, so we can both appreciate the humor of my wearing it.” But… Nick really does LIKE Kelly Clarkson. He respects her as an artist, and is impressed by the production level of her albums. So what is being communicated by his wardrobe? If someone thinks the shirt is funny and ironic, Nick will laugh along and agree that the shirt is “awesome” (a code word for the hip that means everything and nothing at the same time. I use it constantly.) But he will also discuss his appreciation for her music in a separate conversation. Is he communicating two things at once, both the hip irony of wearing something that could be considered uncool, and his sincere appreciation for Kelly? Or is he communicating nothing; or possibly two lies? He respects Kelly Clarkson, but not vehemently enough to refuse humor at her expense. And he conforms to the hip trendiness of the t-shirt coded message, communicating to all in the loop that he knows how this “what’s not cool is cool” thing works, and we’re mutually “in on it”. I’m not sure. It seems like a contradiction. But maybe I’m not hip enough to get it.