The henley sits in an interesting spot in a man’s wardrobe. More considered than a plain tee, less formal than anything with a full collar, it’s the kind of piece that works hardest when you’re not trying to dress up or down but just want to look like you made a decision. The problem is that most of them fail at the basics. The placket puckers after two washes. The fabric goes thin and shapeless. The buttons are cheap and sit crooked. We’ve spent time finding the ones that skip all of that. What we’re looking for is a clean placket that lies flat, a fabric weight that works from early fall through spring layering, and a fit that isn’t trying to be a second skin. The best henleys age well and get better with wear rather than worse. These are the ones we’d reach for on a Saturday and not think twice about.