Go for a black and white vertical striped long sleeve shirt and a white crew-neck t-shirt if you wish to look casually dapper without putting in too much time. If you need to effortlessly step up your getup with a pair of shoes, introduce black leather chelsea boots to this getup. So if you're looking for a look that's dapper but also totally season-appropriate, this one fits the task well. As you can see, as a man in his fifties, you still have a wide range of outfit options.