For an ensemble that's effortlessly elegant and envy-worthy, wear a navy turtleneck and a grey check suit. To give your ensemble a more refined vibe, why not complement your look with a pair of brown leather oxford shoes? So as you can see, it's a killer, not to mention season-appropriate, look to have in your transeasonal collection. Combos like this have a sophisticated air that suit men over 50 very well.