For a look that's very simple but can be flaunted in a variety of different ways, make a navy plaid long sleeve shirt and a white crew-neck t-shirt your outfit choice. For a dressier take, why not throw a pair of black leather derby shoes into the mix? This look is equally neat and season-appropriate. Now we're talking! If you want people to see maturity in you as a young gent, a look like this is a solid bet.