A blazer and olive chinos are indispensable players in any gentleman's collection. On the shoe front, this getup pairs perfectly with black desert boots. In the winter season, when warmth is key, it can be easy to settle for a less-than-stylish outfit. But this outfit is a clear example that you can actually stay warm and remain stylish at the same time in the winter season. Certainly a fail-safe choice if we're talking style tips for gentlemen in their fifties.