This laid-back pairing of a navy barn jacket and blue jeans is very easy to pull together without a second thought, helping you look dapper and prepared for anything without spending a ton of time combing through your wardrobe. A pair of brown leather brogues instantly turns up the wow factor of this ensemble. A neat ensemble that transitions easily into fall like this one makes it super easy to embrace the new season. On a mission for dressing tips for gents in their 50s? This outfit is pretty inspiring.