This combo of a grey plaid overcoat and black chinos is proof that a simple look can still be really interesting. Dress up this look with the help of a pair of dark brown leather derby shoes. So as you can see, this getup is a really good idea, especially for transeasonal weather, when the temperatures are dropping. Perfect to tell people that even as a guy in his 20s you're confident enough to make your own sartorial choices.