I’ve seen this a lot more recently and I’m on the fence about it.

That being said, Boyd Crowder from “Justified” pulls this off extremely well. It somehow makes him look more dangerous than the alternative.

From what I’ve seen in pictures of men who can make this work, there are a couple of rules. First, it should be a blue-collar type work shirt. Something like linen or madras isn’t going to look good buttoned up all the way. Second, it should be consistent with the rest of what you have on. I have a feeling this is a jeans only type application. Third, you can’t hesitate with it. And fourth, you can’t ever ever ever do this: