For a casually classic look, consider wearing a dark brown wool blazer and khaki chinos — these two pieces play really cool together. And if you want to easily polish up this getup with one single item, why not complement your outfit with brown leather chelsea boots? It's a good choice when it comes to piecing together a standout outfit for awkward transition weather. If you often wonder how to dress your age without giving up on fashion, this pairing comes to rescue.