Who Should Wear It: New-school kids who appreciate old-school style.
Why It Works For School: A cool pair of kicks will take your son from home to the classroom to the playground and back again in style.
Our Picks: Velcro closures make the iconic New Balance KE410 sneakers ($50) easy to get on and off. Nike's 6.0 Mogan Mid 2 Jr. Sneaker ($35, originally $55) are the epitome of retro (and, yes, the '80s are retro now) cool. The original Converse Jack Purcell low-tops ($50, available in five colors) have gotten a mod makeover with cool new details. Vans Classic Checker Print Slip-Ons ($23, originally $35) are available in sizes for kids of all ages.