This pairing of a t-shirt and charcoal jeans is a safe and very stylish bet. Bring an elegant twist to an otherwise all-too-common outfit by slipping into a pair of olive leather casual boots. During the winter season, when functionality is imperative, it can be easy to surrender to a less-than-stylish ensemble in the name of convenience. But this ensemble is a bright example that you can actually stay comfortable and remain equally stylish in the winter season. And if we're talking casual fashion tips for middle-aged gentlemen, this combo is perfect.