If you're hunting for a laid-back yet seriously stylish outfit, pair a black and white crew-neck t-shirt with black chinos. Rounding off with casual boots is the simplest way to bring an added dose of sophistication to your outfit. In the winter months, when warmth is crucial, it can be easy to settle for a less-than-stylish look in the name of convenience. But this look is a bright example that you totally can stay warm and remain stylish during the winter months. If you're not sure how to dress your age, this combination is a vivid example.