This combo of a grey plaid double breasted blazer and a black turtleneck is proof that a safe getup doesn't have to be boring. To bring some extra classiness to this look, introduce a pair of black leather derby shoes to the equation. This look is an appealing option if you're hunting for a neat ensemble that transitions easily into fall. This getup is the perfect answer to the question of how to dress your age as you move into your 40s.