The open collar shirt is doing more work in most men’s wardrobes than it gets credit for. It sits in that gap between a smart shirt buttoned to the neck and a casual tee, and when you get it right, the result looks considered without looking like you tried. The problem is most shirts in this space fail on one of two things: the fabric is too stiff to wear relaxed, or the cut is too casual to wear anywhere worth going. We’ve been looking specifically for shirts that move between a Monday meeting and a Saturday evening without needing a different pair of trousers to make them work. Collar roll matters here. So does how the shirt behaves with the top two buttons undone, because that is exactly how you will wear it. We are not interested in shirts that only work tucked in, or only work on holiday. These ones earn their place every week.