As you can see here, it doesn't require that much effort for a man to look casually smart. Consider wearing a navy pea coat and a long sleeve shirt and be sure you'll look awesome. For a more casual aesthetic, why not add brown leather work boots to this getup? You can bet this outfit is great when spring comes. Think you can't pull off cool off-duty outfits as you go into your 50s? This combo should prove you otherwise.