Parade your skills in menswear styling by wearing this off-duty combo of a navy shearling jacket and navy skinny jeans. Rev up the classiness of this outfit a bit with tobacco suede chelsea boots. Putting together a pulled together outfit can be a bit difficult at times on its own. Enter subzero temperatures into the equation, and the whole thing becomes even more difficult. Luckily, this here is your winter inspo. Guys who are curious how to rock smart dressing as you progress through your 20s, you have your answer.