The henley sits in an interesting spot in menswear. More considered than a plain crew neck, less formal than a collared shirt, and when the fit is right it pulls off something that a lot of pieces fail at entirely: it looks like you made a choice. The problem is that too many henleys come in cuts that are either painted on or shapeless, and neither version flatters anyone past their mid twenties. Regular fit is the answer when it is done properly. Not baggy. Not restrictive. Just a clean line through the shoulder and chest that works tucked, untucked, under an overshirt, or on its own in warmer weather. We have been particularly focused on fabric quality here because a henley lives and dies by how well it drapes and how it holds up after washing. The button placket detail should look intentional, not decorative. These are the ones that get the balance right.