Pair a black trenchcoat with a white and black print crew-neck t-shirt and you'll be the picture of rugged sophistication. You can stick to the classic route in the shoe department by finishing off with loafers. This one is an exciting choice when it comes to a cool summer-to-fall outfit. If you want to portray maturity and professionalism as a man in his 20s, an ensemble like this is what you're looking for.