This laid-back pairing of a navy henley shirt and dark brown chinos is extremely easy to throw together without a second thought, helping you look amazing and ready for anything without spending a ton of time combing through your closet. Our favorite of an endless number of ways to finish this getup is with a pair of black and white check canvas slip-on sneakers. This combination should encourage anyone who had doubts about donning casual outfits as a guy in his forties.