The overshirt gets misused more than almost any other piece in menswear. Worn too fitted and it looks like a work shirt that missed the memo. Worn too oversized without intention and it reads shapeless. The sweet spot is an oversized cut that’s been properly thought through, where the shoulders sit just right, the fabric has enough body to drape rather than hang, and the length works over whatever you’re wearing underneath. We’ve been paying close attention to how these pieces actually sit on a real body rather than a mannequin. The ones worth your money have structure built into the fabric weight itself, so you’re not relying on a perfect tuck or a specific layer to make them work. Brushed cotton, heavy flannel, and garment washed twill are the materials doing the heavy lifting here. Wear them open over a tee or closed as a light outer layer. These are the ones that flatter without requiring any effort on your part.