For something on the off-duty side, consider pairing a blue bomber jacket with light blue chinos. You can take a more laid-back approach with shoes and complete this look with athletic shoes. This one will play especially well come warmer days. And if we're talking casual dressing ideas for 50-year-old gentlemen, this combo looks good on almost any gent.
This casually cool outfit is easy to break down: a blue bomber jacket and olive chinos. Introduce a pair of athletic shoes to the mix to bring a dash of stylish casualness to this ensemble. So so as you can see, it's a sharp, not to mention season-appropriate, ensemble to keep in your transeasonal rotation. A fail-safe option ensemble appropriate for guys in their 50s who prefer casual dressing.