Go for a pared down but at the same time cool and casual option by marrying an olive shirt jacket and navy jeans. Here's how to play it up: derby shoes. If you're on the hunt for an easy-to-transition outfit, this one fits the task well. As you're progressing through your teens, you probably want to start dressing more like a grown-up. In this case, outfits like this become a great source of inspiration.