This classic and casual combination of a black overcoat and a crew-neck t-shirt is extremely easy to throw together without a second thought, helping you look sharp and ready for anything without spending too much time searching through your wardrobe. Take your getup down a dressier path by slipping into a pair of black leather chelsea boots. This combo shows that looking fashionable as a 30-something Millennial gentleman is not that daunting a task.