As you can see here, it doesn't require that much effort for a man to look effortlessly neat. Team a trenchcoat with black jeans and you'll look awesome. Why not complement your look with a pair of low top sneakers for a playful vibe? When it's one of those bleak fall afternoons, what better to spice it up than a stylish outfit like this one? Guys wondering how to pull off modern casual dressing as you progress through your 20s, this outfit should answer your question.