Wearing your work clothes is all about the weather and the terrain. The only obstacle to wearing your work clothes is typically getting them all sweaty. If the weather is cool and not inclement, then that's not an issue. The only deterrence after that is not riding through mud puddles. I've don't it many times in the winter and fall but not in the summer, and not in the southeast. During those dog days, I'd sweat through a t-shirt within two blocks.