If you gravitate towards relaxed casual style, why not opt for this combination of a shirt jacket and a hoodie? Puzzled as to how to round off your look? Wear brown suede casual boots to lift it up. Surely a surefire option if we're talking style for gentlemen in their fifties.
A shirt jacket and a hoodie are the kind of a winning casual ensemble that you need when you have no extra time to plan out an ensemble. For something more on the elegant side to finish off this ensemble, add a pair of brown suede derby shoes to the mix. With a look like this, any middle-aged man is bound to put the younger generation to shame.