When the dress code calls for an effortlessly classy ensemble, make a navy trenchcoat and a long sleeve shirt your outfit choice. You could perhaps get a bit experimental in the footwear department and add a pair of charcoal athletic shoes. A knockout summer-to-fall outfit like this one makes it extremely easy to embrace the new season. Think it's hard for 40-year-old guys to master edgy off-duty dressing? This combo will prove you otherwise.