This casual combo of a black bomber jacket and grey jeans is very easy to put together in next to no time, helping you look on-trend and prepared for anything without spending too much time going through your wardrobe. For something more on the classy end to finish this look, add a pair of black suede chelsea boots to this outfit. This one is an obvious idea when it comes to a kick-ass ensemble that transitions easily into fall. Wondering how to dress after forty? This combo is the perfect answer.