This refined combo of an overcoat and black wool dress pants is a frequent choice among the trendsetting chaps. To bring a sense of stylish casualness to this ensemble, introduce a pair of low top sneakers to your outfit. During winter, when functionality is top priority, it can be easy to surrender to a less-than-stylish ensemble. But this ensemble is a stark illustration that you can actually stay toasty and remain equally stylish in winter. This combo demonstrates that dressing stylishly as a gent in his thirties is totally doable.