For a casually sleek ensemble, try pairing a blue chambray dress shirt with black jeans — these items work really good together. On the fence about how to complete this look? Wear a pair of dark brown leather double monks to ramp up the style factor. If you're already bored of your transitional weather fashion options, this ensemble just might be the inspo you are searching for. This pairing proves that hitting 40 is no reason to drop your dressing standards.