Make a black crew-neck t-shirt and charcoal ripped jeans your outfit choice if you're scouting for an outfit idea that conveys urban style. For something more on the classier end to complement this look, complement your ensemble with a pair of white canvas low top sneakers. As you can see, it's very easy to look awesome and stay cozy come fall, all thanks to outfits like this. Those wondering how to stay stylish as you move into your 40s, you have your answer.