Go for something casual yet trendy in a blue denim jacket and navy ripped jeans. And if you need to easily up the style ante of this getup with a pair of shoes, introduce a pair of black leather chelsea boots to the mix. As you can see, it's extremely easy to look awesome and stay comfy when chillier days are here, all thanks to combinations like this one. Off-duty ensembles for stylish 50-year-old gentlemen aren't actually that hard, as you can see.