To pull together an off-duty menswear style with a modern twist, dress in a black shearling jacket and chinos. Up your look by rounding off with charcoal athletic shoes. In the colder months, when comfort is critical, it can be easy to settle for a less-than-stylish look in the name of functionality. However, this look is a practical illustration that you can actually stay warm and remain stylish in the colder months. Wondering how to nail casual style in your late 20s? This pairing is a practical example.