A crew-neck t-shirt and blue jeans will convey this relaxed and dapper vibe. Let your sartorial chops truly shine by complementing this ensemble with a pair of navy and white athletic shoes. In the colder months, when comfort is paramount, it can be easy to settle for a less-than-stylish look. But this look is a striking example that you totally can stay comfortable and remain equally stylish during the colder months. Think gentlemen in their 50s can't pull off cool casual dressing? This combination is definitive proof of otherwise.