The overshirt should be one of the easiest things in a wardrobe to get right. Layer it over a tee, wear it open like a jacket, button it up and tuck it in. The problem is that most of them are cut for a body type that does not exist, or made in fabrics so stiff they never drape properly, or sized in a way that relaxed becomes shapeless. That last one is where most men get tripped up. Relaxed fit is not the same as wearing something two sizes too big. There is a specific thing that happens when an overshirt is cut correctly: it looks effortless without looking like you stopped caring. We have been looking specifically for pieces that hit that mark, in weights that work through three seasons, and in colors that actually integrate with a real wardrobe rather than just photograph well. These are the ones that earn the layering real estate.