Clifford asks: My new question for you is, what are your thoughts on short sleeve dress shirts for the hotter months? Yay or Nay? I very seldom see anyone pull this off without looking like Homer Simpson.
In general: nay. However, it can be done.
You should never wear a short-sleeved dress shirt the way Homer does: as a substitute for a long-sleeved dress shirt. Best case scenario is you look like a Mormon missionary, and worst case scenario, you look like something that’s even worse than that (nothing coming to mind right now).
However, it is possible to wear a short sleeved button-up shirt in a more casual context and not look like a dweeb. First of all, fit will make a huge impact. A slim fit here is even more important than usual because it sends the message: “this is a choice I’m making." Your goal is to be clear that the short sleeves aren’t just a concession to the heat and slobbiness, but rather an affirmative action. The second thing to remember is that you’re looking for a casual shirt. Something like this gingham button-down from Black Fleece is a good example. A casual pattern, a casual fabric, a casual collar style and a sharp fit (at least on the not-very-skinny folks like me).
It should also be paired with clothes that fit you well. The goal, again, is to have an ensemble that gives people the feeling that you know what you’re doing, which will allay their fears that you are Homer Simpson.
