This laid-back combo of a black denim shirt jacket and black jeans is ideal when you need to look good but have no extra time to dress up. Finishing off with black leather derby shoes is a guaranteed way to bring an extra dimension to your look. As the weather starts to cool down, you'll see that an outfit like this is perfect for the season. Wondering how to dress your age as you get into your 50s? This ensemble is the perfect answer.