Opt for a blazer and black jeans if you're aiming for a proper, dapper outfit. Why not introduce low top sneakers to your ensemble for a fun feel? During winter, when warmth is the priority, it can be easy to settle for a less-than-stylish look in the name of practicality. But this look proves that you totally can stay cozy and remain stylish in winter. This outfit shows that as a 50-year-old gentleman, you still have a wide range of style options.