What we have here is a complex dichotomy of two different personal statements happening at the same time. The baseball cap and the t-shirt which proclaims this gentleman to be a 'smooth talker' and a 'straight shooter' say that he's about as straight-laced as straight-laced could possibly be. As for what's going on with his lower torso; well, that's a completely different story.
Underwear doesn't have to be gender-specific, and so we're all free to wear whatever makes us happy down there. We just aren't convinced that this is making him all that happy. To our eyes, it looks like he's dealing with a particularly uncomfortable wedgie. Perhaps he's on the phone to his wife, asking if there was some kind of mistake made when the fresh washing was handed out that morning. We're sure he could handle any question anyone asked of him about his clothing choices though - he is, after all, a smooth talker.