Outdoor Research Solstice Bucket Hat - Boys' - $11.98

Before he heads out to the trail, toss your not-so-little-anymore guy the Outdoor Research Boy's Solstice Bucket Hat. Its SolarShield construction and UPF-30-rated fabric helps prevent the sun from hammering his head. A TransAction headband wicks moisture off his brow, while this lightweight hat's design helps keep him cool all day long. - $11.98