Wear a white and navy dress shirt with grey dress pants and you will surely make heads turn. Want to dial it down on the shoe front? Introduce a pair of black leather derby shoes to the equation for the day. Planning a standout combination can be a bit of a conundrum on its own. Enter extra cold temperatures into the equation, and the whole thing becomes even more difficult. Luckily, this here is your winter outfit inspiration. As as a teenage boy slipping into your 20s, this is how you dress fashionably and look a little older than your age.