This relaxed combo of a dark brown leather bomber jacket and a black long sleeve t-shirt is super easy to throw together without a second thought, helping you look amazing and prepared for anything without spending too much time searching through your wardrobe. Switch up your ensemble by finishing with a pair of black leather derby shoes. Seeing as temps are falling, this look appears a viable pick for the time in between seasons. Guys who wonder how to sport smart casual dressing in your twenties, you have your answer.