This laid-back combo of a dark brown houndstooth wool blazer and dark green cargo pants is very easy to throw together without a second thought, helping you look on-trend and prepared for anything without spending too much time searching through your closet. When in doubt about what to wear when it comes to shoes, stick to desert boots. Rest assured, this look will keep you snug as well as looking stylish in this in-between weather. This one is a stylish and age-appropriate outfit for mature guys.