A varsity jacket and a red and black long sleeve shirt married together are a match made in heaven for gentlemen who appreciate laid-back styles. To give your outfit a more refined twist, why not complement your look with black leather double monks? When it's one of those gloomy fall days, sometimes only a cool look like this one can get you out the door in the morning. This is a combo you, as a gent in his 50s, can always count on.