A bomber jacket and grey wool chinos are a combination that every modern gent should have in his off-duty styling routine. Complete this getup with a pair of navy low top sneakers to keep the outfit fresh. In winter, when warmth is everything, it can be easy to settle for a less-than-stylish ensemble in the name of functionality. But this ensemble is a bright example that you can actually stay comfortable and remain stylish at the same time in winter. Outfits like this have a refined air that suit men over 30 really well.