Why not make a navy denim jacket and grey chinos your outfit choice? These two pieces are super practical and look amazing paired together. Take your ensemble in a more elegant direction with black leather chelsea boots. So if you're hunting for a look that's stylish but also feels totally season-appropriate, this just might be it. As you're moving through your late 20s, you want to start dressing more like a mature gentleman. In this case, ensembles like this are a tested option.