The open collar shirt is one of the most deceptively difficult things to get right in a man’s wardrobe. Wear a bad one unbuttoned and you look like you’ve forgotten to finish getting dressed. Wear the right one and it does more work than most men give it credit for, carrying a smart casual evening, a weekend lunch, a summer wedding where the jacket comes off by three in the afternoon. The category gets let down by shirts that are built for the boardroom and just have their top button undone. That is not what we are looking for here. We want shirts where the open collar is the intention, where the fabric drapes rather than gaps, and where the construction holds up when it is worn in rather than looking tired after two outings. Fabric weight matters. Collar spread matters. The way it sits over a trouser waistband matters. These ones have thought about all of it.