Combining a grey plaid overcoat and a black crew-neck sweater is a guaranteed way to inject your closet with some relaxed sophistication. For something more on the classier end to round off this ensemble, add a pair of black leather tassel loafers to the equation. This one is an obvious idea when it comes to a kick-ass outfit that will take you from summer to fall. Think it's hard for men in their 20s to nail semi-casual dressing? This pairing will prove you otherwise.