Most shorts look worse the more you wear them. Linen is the exception. A good pair of linen shorts softens, relaxes, and settles into something that looks like it belongs on you rather than on a rack. That earned quality is exactly what we were looking for here. The problem most men run into is buying linen shorts that are either too long, too baggy, or made from fabric so thin it loses its structure by noon. We have been looking specifically at cuts that sit at the right point on the thigh and fabric weights that hold their shape in heat without feeling stiff. The color matters too. We have favored the tones that work with an open collar shirt and a sandal as easily as they do with a polo and a loafer. Linen rewards patience. Buy the right pair once and they will look better in three years than they do today.