Today’s Tip of the Day: Don’t wear short sleeve, button down dress shirts (especially with ties). You will look like Michael Bolton from Office Space, and that is not a look you want to aim for: Often times I see the “Dad” generation wearing Tommy Bahama or some similar brand of button down dress shirts that they leave untucked. I am not going to start taking shots because I’m fairly certain I know a plethora of older men who do so, but it is NEVER a look that I am going to promote.
If the weather is warm and you want to look dressy but don’t feel like rocking the long sleeve button down, I think there are many better options than this look. Even if you are a big guy, there are slimmer versions of shirts in this style category that will look better on you. I’m a big fan of Polo shirts and rolling of sleeves, but you won’t catch me rocking the Michael Bolton look any time soon.