A navy harrington jacket and a black crew-neck t-shirt will give off this relaxed and dapper vibe. Black and orange athletic shoes will bring a dash of stylish nonchalance to an otherwise mostly dressed-up look. As you can see, this combo is a really nice idea, especially for transeasonal weather, when the temperatures are falling. Laid-back looks for 60-something gentlemen aren't actually that hard, as you can see.