This casually cool outfit is super simple: a brown windbreaker and charcoal vertical striped chinos. Clueless about how to complement this ensemble? Round off with brown leather desert boots to smarten it up. As you can see, it's super easy to look stylish and stay comfy come colder weather, all thanks to ensembles like this one. An ensemble like this will make any gentleman over 40 look better than everyone else in the room.