A crew-neck sweater and a navy turtleneck? This is an easy-to-style outfit that you can rock a version of on a daily basis. Black leather derby shoes will breathe an extra dose of style into an otherwise too-common getup. On not-so-bone-chilling afternoons, you can wear this transitional look and look absolutely awesome. A look like this can make any guy in his forties look better than everyone else in the room.