Wear a barn jacket and khaki chinos for a simple ensemble that's also put together. For something more on the classy end to finish your look, add a pair of derby shoes to the mix. So if you're looking for an amazing transition look, this one is great. As you're transitioning from a kid to an adolescent, you probably want to start dressing more like an adult. That's when outfits like this are a fail-safe option.