A grey plaid overcoat and white dress pants are absolute wardrobe heroes if you're planning a classy wardrobe that holds to the highest sartorial standards. If in doubt as to what to wear when it comes to footwear, finish with a pair of brown leather derby shoes. You see that just because it's freezing outside doesn't mean your combinations can't be both warm and seriously stylish. On a mission for outfit ideas for over-30 gentlemen? This combo should go straight to your favorites.