"I recently came across your site and have been a fan ever since. I have a style related question that I was hoping you could answer for me: Is it fashionable to wear a short sleeve button down shirt over a blazer? It sounds like potential combination in my head but short sleeves always remind me of Dwight from The Office. What's your take?" - Kyle We admit this is a new one for us. We weren't sure if you actually meant what you wrote or something else but we'll take it head on. The short answer to your question is a definite no. You should never wear or think about wearing a short sleeved button up shirt over a blazer. We actually had a hard time even thinking how this would be anatomically possible in terms of comfort and function.Then we got to thinking where we may have seen something like this before. Sure enough this Lacoste ad popped up. This happens to be done a bit different. It's a polo shirt over a suit but its the same concept. It doesn't look good on a model in a major ad and it won't look good on you either. We suggest finding a different way to express yourself other than wearing shirts over your blazer when they most certainly belong under it.