This classic and casual pairing of a navy overcoat and black jeans is extremely easy to throw together without a second thought, helping you look awesome and ready for anything without spending too much time searching through your wardrobe. Feeling bold? Change up this outfit with red canvas low top sneakers. An amazing transition outfit like this one makes it super easy to welcome the new season. Dressed like this, any middle-aged man will put many a younger man to shame.