When it comes to high-octane dapper style, this combination of an orange crew-neck sweater and blue wool dress pants is the ultimate style. Brown suede desert boots will add a more laid-back feel to an otherwise all-too-safe getup. Figuring out a pulled together look can be challenging on its own. Add cold temperatures into the equation, and the whole thing becomes even more difficult. Luckily, this here is your wintry outfit inspo. So as you can see, as a middle-aged gentleman, you still have a wide range of styling options.