Marry an orange windbreaker with navy jeans if you wish to look casually dapper without much effort. To introduce an extra dimension to this ensemble, introduce dark brown leather casual boots to your getup. As you can see, it's super easy to look dapper and stay snug when chillier weather arrives, all thanks to ensembles like this. Think it's hard for 40-year-old gents to master cool off-duty looks? This combo will prove you wrong.