A brown trenchcoat and dark brown plaid chinos are a pairing that every sharp gent should have in his wardrobe. And if you wish to easily up the style ante of this ensemble with footwear, add a pair of derby shoes to your outfit. This combination is an excellent choice when it comes to a kick-ass look that will take you from summer to fall. When it comes to fashion tips for over-40 gents, this getup looks nice on most guys.