This pairing of a trenchcoat and a navy denim shirt can only be described as seriously dapper and effortlessly classy. And if you wish to effortlessly dress down this ensemble with one single piece, introduce a pair of black and white canvas high top sneakers to this look. On not-so-bone-chilling days, you can rock this easy-to-transition outfit and look absolutely amazing. A cool, less conservative combination for over-30 men.