This is solid proof that a white dress shirt and black dress pants look amazing when paired up in a sophisticated look for today's gentleman. If not sure as to what to wear when it comes to footwear, complete this outfit with tobacco suede oxford shoes. This ensemble is a great choice if you're crafting a well-coordinated look for awkward transition weather. If you're wondering how you should dress as a middle-aged gent, this outfit gives a proper idea.