Combining a black crew-neck t-shirt with black leather jeans is an amazing pick for a casually cool getup. Introduce black leather chelsea boots to the mix to immediately dial up the fashion factor of any look. So as you can see, this outfit is a really wonderful choice, especially for weird fall weather, when the temperature is dipping. Wondering how to dress age-appropriately as you get into your 40s? This combo is the perfect answer.