This pairing of an olive bomber jacket and a grey crew-neck t-shirt is the perfect foundation for a multitude of combinations. To inject a more casual feel into this ensemble, complete your ensemble with a pair of white canvas high top sneakers. Seeing as it is getting chillier with each day, this ensemble seems a viable choice for the season. Laid-back outfits for stylish men in their forties aren't actually that hard, as you see.