This outfit with a black bomber jacket and a blazer isn't hard to score and easy to change. To add an air of stylish casualness to your getup, complete this look with a pair of brown athletic shoes. Rest assured, this outfit will keep you toasty as well as looking seriously stylish in this summer-to-fall weather. As you mature into your 30s, you probably want to start dressing like an adult. That's when getups like this are a surefire option.