This combination of a charcoal wool blazer and a charcoal turtleneck looks considered and makes you look instantly cooler. Does this ensemble feel all-too-dressy? Introduce brown leather work boots to change things up a bit. While dressing for winter can be a bit difficult at times, it's ensembles like this that make you feel inspired. And if we're talking casual style for middle-aged guys, this getup looks cool on almost any gent.