This pairing of a blazer and a beige turtleneck is proof that a safe look can still be seriously dapper. A trendy pair of black leather chelsea boots is an effective way to upgrade your outfit. In the colder months, when warmth is above all, it can be easy to settle for a less-than-stylish getup in the name of convenience. But this getup is a stark illustration that you can actually stay snug and remain stylish at the same time during the colder months. If you're wondering what you should wear as an older guy, this pairing gives a proper idea.