This laid-back combination of a beige bomber jacket and black skinny jeans is very easy to throw together without a second thought, helping you look awesome and prepared for anything without spending too much time digging through your wardrobe. In the footwear department, go for something on the dressier end of the spectrum by finishing off with black leather casual boots. This ensemble should clear any doubts you had about wearing casual clothes as a guy in his 50s.