Infuse a dash of laid-back sophistication into your day-to-day styling lineup with a white crew-neck t-shirt and grey wool dress pants. Let your sartorial chops truly shine by finishing off this look with brown leather dress boots. In the winter months, when warmth is crucial, it can be easy to settle for a less-than-stylish look. But this look is a striking example that you totally can stay snug and remain stylish at the same time during the winter months. Gents who wonder how to dress fashionably and look good as you progress through your 20s, you have your answer.