If you feel more confident wearing something functional, you'll love this dapper combination of a denim jacket and a short sleeve shirt. You can get a bit experimental in the shoe department and introduce a pair of black leather tassel loafers to the equation. Piecing together a cool look can be a bit nerve-racking and time consuming on its own. Enter below-freezing temps into the equation, and the whole thing becomes even more difficult. No worries, this here is your winter outfit inspo. Guys who are curious how to stay stylish as you turn 30, you have your answer.