Wear a black crew-neck t-shirt with charcoal ripped jeans for an off-duty and trendy look. On the shoe front, go for something on the smarter end of the spectrum and complement this outfit with white canvas low top sneakers. Rest assured, this combination will keep you snug as well as looking stylish in this weird fall weather. Think it's hard for men in their forties to perfect modern off-duty dressing? This combo should prove you otherwise.