For an off-duty look without the need to sacrifice on practicality, we turn to this pairing of a black and white bomber jacket and light blue ripped jeans. Rounding off with black suede chelsea boots is the simplest way to bring some extra flair to your getup. If you're hunting for a kick-ass ensemble that will take you from winter to spring, this just might be it. Gentlemen who wonder how to dress well as you go into your 50s, you have your answer.