A tan trenchcoat and a black turtleneck are absolute mainstays if you're picking out an elegant wardrobe that holds to the highest menswear standards. Spice up this look with a more elegant kind of shoes, such as this pair of burgundy leather derby shoes. When it comes to dressing for fall, nothing beats a kick-ass combination that transitions easily between seasons. This is a perfect example of how to dress stylishly and look age-appropriate.