This getup proves that it pays to invest in such menswear must-haves as a camel overcoat and a black knit turtleneck. If you wish to easily smarten up your ensemble with one single piece, introduce a pair of grey suede chelsea boots to this outfit. There's no nicer way to brighten up a dull autumn afternoon than a killer ensemble like this one. This pairing demonstrates that figuring out how to dress well as a guy in his 50s is not particularly hard.