One of the classiest ways to style such a timeless menswear item as a charcoal waistcoat is to marry it with a navy suit. And if you wish to effortlessly tone down this look with one item, complete this ensemble with a pair of double monks. When it comes to dressing for autumn, nothing beats a knockout ensemble that transitions easily between seasons. This combination demonstrates that dressing cool as you make your way through your 20s is not that daunting a task.