This laid-back pairing of a black leather harrington jacket and jeans is very easy to pull together in no time flat, helping you look seriously stylish and prepared for anything without spending too much time rummaging through your wardrobe. For a more relaxed feel, complete your look with black and blue athletic shoes. As you can see, it's extremely easy to look amazing and stay comfortable come fall, all thanks to combos like this one. All in all, an ideal demonstration of relaxed casual style for over-40 gentlemen.