A light blue dress shirt and dark green corduroy dress pants are a classy getup that every stylish man should have in his sartorial arsenal. Complement this outfit with dark brown leather derby shoes to instantly step up the street cred of your ensemble. So as you can see, it's a dapper, not to mention season-appropriate, outfit to keep in your transeasonal rotation. No doubt, a wonderful pick when it comes to outfit ideas for 50-something men.