For relaxed refinement with a rugged take, you can go for an overcoat and a black long sleeve shirt. Tan suede cowboy boots will add a sense of stylish effortlessness to an otherwise all-too-safe look. When it's one of those dreary fall days, sometimes only a kick-ass ensemble like this one can get you out the door in the morning. If you're not sure how to dress as a 20-year-old gent, this getup is a perfect example.