The pairing of a dress shirt and red and black plaid chinos makes for a really well-executed outfit. Add black casual boots to the equation et voila, the ensemble is complete. Keep this ensemble in your front hall wardrobe when spring sets it, and we guarantee you'll save a lot of time planning what to wear on more than one morning. As you're transitioning from a kid to a teenage boy, you probably want to look older. That's when outfits like this are a tested option.