Infuse personality into your current casual routine with an olive military jacket and a blue denim shirt. And if you need to immediately play down this outfit with a pair of shoes, why not complete your look with a pair of grey athletic shoes? As you can see here, it's extremely easy to look dapper and stay cozy come chillier weather, thanks to this getup. Think it's hard for guys in their 40s to master cool off-duty dressing? This combination will prove you otherwise.