This pairing of a sweatshirt and black skinny jeans epitomizes laid-back attitude and casual menswear style. To bring some extra classiness to this look, complete this look with a pair of black casual boots. In the colder months, when practicality is crucial, it can be easy to surrender to a less-than-stylish ensemble. This ensemble, however, is a good illustration that you totally can stay comfortable and remain stylish in the colder months. Gents wondering how to pull off cool casual style as you progress through your 20s, this combo should answer your question.