You'll be surprised at how extremely easy it is for any gentleman to put together this effortlessly smart ensemble. Just a bomber jacket matched with a dress shirt. Feeling adventerous? Spice things up by rocking a pair of black leather chelsea boots. There's no better way to spice up a gloomy fall afternoon than a stylish ensemble like this one. This combo illustrates that even well into your 50s your style options are still far from limited.