Infuse an elegant touch into your current arsenal with an overcoat and a gilet. For times when this outfit looks too polished, dress it down by wearing a pair of grey suede desert boots. While it can be a bit of a juggling act to stay on-trend in below-freezing temperatures, it's combos like this that prove it's actually possible. Guys who are curious how to dress fashionably and look good as you go through your teenage years, you have your answer.