Marry a charcoal crew-neck t-shirt with black skinny jeans for comfort dressing with a street style finish. Throw dark brown suede casual boots in the mix to avoid looking too casual. In the winter months, when functionality is everything, it can be easy to surrender to a less-than-stylish outfit in the name of functionality. However, this outfit is a practical illustration that you totally can stay toasty and remain equally stylish during the winter months.