Such items as a black cardigan and a white crew-neck t-shirt are an easy way to infuse effortless cool into your day-to-day casual lineup. To introduce some extra depth to this outfit, throw a pair of dark brown leather derby shoes into the mix. If you're on the hunt for a killer outfit that transitions easily into spring, this just might be it. Casual outfits for middle-aged men aren't actually that hard, as you can see here.