Go for a polo and khaki dress pants and you'll achieve a proper and classy outfit. You can get a little creative in the shoe department and dial down this outfit with brown desert boots. Putting together a well-coordinated outfit can be a bit difficult at times on its own. Enter extra cold temperatures into the equation, and the whole thing becomes even more difficult. Fear not, this here is your wintry inspo. This combination illustrates how to look good after fifty.