If the situation permits a relaxed casual look, opt for a denim jacket and a white and blue short sleeve shirt. If you want to feel a bit more elegant now, add a pair of black leather tassel loafers to your look. In the winter months, when warmth is a must, it can be easy to settle for a less-than-stylish ensemble in the name of practicality. However, this ensemble is a stark illustration that you totally can stay cozy and remain stylish at the same time in the winter months. This combo shows that looking fashionable as a gent in his thirties is quite manageable.