For an outfit that's super straightforward but can be flaunted in plenty of different ways, consider teaming a black crew-neck t-shirt with grey chinos. Rounding off with black leather derby shoes is a surefire way to infuse a dose of class into this getup. When spring is here, you'll love this ensemble as your go-to for in-between weather. Looking for dressing tips for 40-something gentlemen? This getup is great inspiration.