If the situation permits a casual ensemble, consider teaming a grey crew-neck t-shirt with grey jeans. Black and white canvas low top sneakers complete this getup very well. Those who are curious how to dress fashionably as you pass the big 4-0, you have your answer.
This combination of a grey crew-neck t-shirt and grey vertical striped shorts is hard proof that a safe casual outfit can still be really stylish. Look at how great this ensemble pairs with a pair of black and white canvas low top sneakers. Think it's hard for middle-aged gents to master modern off-duty dressing? This combination is definitive proof of otherwise.